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5-Hydroxymethylpyrrolidin-2-one, also known as (R)-5-(Hydroxymethyl)-2-pyrrolidinone, is a 2-pyrrolidone derivative with therapeutic applications as a prostanoid receptor agonist. It is a chiral compound with a hydroxymethyl group attached to the 5-position of the pyrrolidinone ring, which plays a crucial role in its biological activity.

66673-40-3

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66673-40-3 Usage

Uses

Used in Pharmaceutical Industry:
5-Hydroxymethylpyrrolidin-2-one is used as a prostanoid receptor agonist for the treatment of various medical conditions. It modulates the activity of prostanoid receptors, which are involved in a wide range of physiological processes, including vasodilation, bronchodilation, and platelet aggregation inhibition. This makes it a potential therapeutic agent for conditions such as cardiovascular diseases, respiratory disorders, and thrombotic disorders.
Additionally, 5-Hydroxymethylpyrrolidin-2-one can be used in drug development as a lead compound for the synthesis of other bioactive molecules with potential therapeutic applications. Its unique structure and functional groups allow for further chemical modifications to enhance its pharmacological properties and target specificity.

Check Digit Verification of cas no

The CAS Registry Mumber 66673-40-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 6,6,6,7 and 3 respectively; the second part has 2 digits, 4 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 66673-40:
(7*6)+(6*6)+(5*6)+(4*7)+(3*3)+(2*4)+(1*0)=153
153 % 10 = 3
So 66673-40-3 is a valid CAS Registry Number.
InChI:InChI=1/C5H9NO2/c7-3-4-1-2-5(8)6-4/h4,7H,1-3H2,(H,6,8)/t4-/m1/s1

66673-40-3 Well-known Company Product Price

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  • TCI America

  • (H1241)  (R)-5-(Hydroxymethyl)-2-pyrrolidinone  >98.0%(GC)(N)

  • 66673-40-3

  • 1g

  • 280.00CNY

  • Detail
  • TCI America

  • (H1241)  (R)-5-(Hydroxymethyl)-2-pyrrolidinone  >98.0%(GC)(N)

  • 66673-40-3

  • 5g

  • 890.00CNY

  • Detail
  • Alfa Aesar

  • (L18358)  (R)-(-)-5-(Hydroxymethyl)-2-pyrrolidinone, 99%   

  • 66673-40-3

  • 1g

  • 439.0CNY

  • Detail
  • Alfa Aesar

  • (L18358)  (R)-(-)-5-(Hydroxymethyl)-2-pyrrolidinone, 99%   

  • 66673-40-3

  • 5g

  • 1752.0CNY

  • Detail
  • Aldrich

  • (366358)  (R)-(−)-5-(Hydroxymethyl)-2-pyrrolidinone  99%

  • 66673-40-3

  • 366358-1G

  • 469.17CNY

  • Detail
  • Aldrich

  • (366358)  (R)-(−)-5-(Hydroxymethyl)-2-pyrrolidinone  99%

  • 66673-40-3

  • 366358-5G

  • CNY

  • Detail

66673-40-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name (R)-(-)-5-(Hydroxymethyl)-2-pyrrolidinone

1.2 Other means of identification

Product number -
Other names (5R)-5-(hydroxymethyl)pyrrolidin-2-one

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:66673-40-3 SDS

66673-40-3Synthetic route

(R)-N-(tert-butoxycarbonyl)-5-(tert-butoxymethyl)pyrrolidin-2-one

(R)-N-(tert-butoxycarbonyl)-5-(tert-butoxymethyl)pyrrolidin-2-one

(R)-5-hydroxymethylpyrrolidin-2-one
66673-40-3

(R)-5-hydroxymethylpyrrolidin-2-one

Conditions
ConditionsYield
With water; trifluoroacetic acid In dichloromethane at 50℃; for 5h;99%
methyl (2R)-pyroglutamate
64700-65-8

methyl (2R)-pyroglutamate

(R)-5-hydroxymethylpyrrolidin-2-one
66673-40-3

(R)-5-hydroxymethylpyrrolidin-2-one

Conditions
ConditionsYield
With methanol; sodium tetrahydroborate at 0℃;97%
With methanol; sodium tetrahydroborate at 0℃;97%
With methanol; sodium tetrahydroborate at 0℃;97%
ethyl (R)-2-pyrrolidone-5-carboxylate
68766-96-1

ethyl (R)-2-pyrrolidone-5-carboxylate

(R)-5-hydroxymethylpyrrolidin-2-one
66673-40-3

(R)-5-hydroxymethylpyrrolidin-2-one

Conditions
ConditionsYield
With lithium borohydride In tetrahydrofuran for 16h; Ambient temperature;85%
With sodium tetrahydroborate In tetrahydrofuran; methanol at 5℃; for 1h;80%
With sodium tetrahydroborate In ethanol for 2h; Ambient temperature;79%
D-pyrrolidone-5-carboxylic acid
4042-36-8

D-pyrrolidone-5-carboxylic acid

(R)-5-hydroxymethylpyrrolidin-2-one
66673-40-3

(R)-5-hydroxymethylpyrrolidin-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 94 percent / SOCl2 / 1.5 h / 80 °C
2: 85 percent / LiBH4 / tetrahydrofuran / 16 h / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: 95 percent / thionyl chloride / 1.) 0 deg C, 30 min, 2.) room temp., 3 h
2: 78 percent / NaBH4 / ethanol / 2 h / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: SOCl2 / 48 h / Ambient temperature; pH=0
2: 58 percent / NaBH4 / propan-2-ol / 20 h / Ambient temperature
View Scheme
D-Glutamic acid
6893-26-1

D-Glutamic acid

(R)-5-hydroxymethylpyrrolidin-2-one
66673-40-3

(R)-5-hydroxymethylpyrrolidin-2-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 1) thionyl chloride / 1a) room temp., 1 h, 1b) reflux, 30 min.
2: 32.5 g / 1.5 h / 150 °C / 15 Torr
3: 79 percent / sodium borohydride / ethanol / 2 h / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: 88 percent / SOCl2, KOH / 150 °C
2: LiBH4
View Scheme
Multi-step reaction with 3 steps
1: H2O / 63 h / Heating
2: SOCl2 / 48 h / Ambient temperature; pH=0
3: 58 percent / NaBH4 / propan-2-ol / 20 h / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1.1: thionyl chloride
1.2: Amberlyst A-21
1.3: Reflux
2.1: sodium tetrahydroborate / isopropyl alcohol
View Scheme
Multi-step reaction with 2 steps
1.1: thionyl chloride / 20 h / 20 °C
1.2: 2 h / Reflux
2.1: sodium tetrahydroborate / isopropyl alcohol / 20 h / 20 °C
View Scheme
D-glutamic acid diethyl ester
13107-55-6

D-glutamic acid diethyl ester

(R)-5-hydroxymethylpyrrolidin-2-one
66673-40-3

(R)-5-hydroxymethylpyrrolidin-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 32.5 g / 1.5 h / 150 °C / 15 Torr
2: 79 percent / sodium borohydride / ethanol / 2 h / Ambient temperature
View Scheme
D-glutamic acid dimethyl ester hydrochloride
13515-99-6, 23150-65-4, 27025-25-8

D-glutamic acid dimethyl ester hydrochloride

(R)-5-hydroxymethylpyrrolidin-2-one
66673-40-3

(R)-5-hydroxymethylpyrrolidin-2-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: toluene / 4 h / Reflux
2: isopropyl alcohol; sodium tetrahydroborate / 20 h / 20 °C
View Scheme
(R)-5-hydroxymethylpyrrolidin-2-one
66673-40-3

(R)-5-hydroxymethylpyrrolidin-2-one

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

(R)-5-(((tert-butyldimethylsilyl)oxy)methyl)pyrrolidin-2-one
128899-30-9, 100548-49-0, 106191-02-0

(R)-5-(((tert-butyldimethylsilyl)oxy)methyl)pyrrolidin-2-one

Conditions
ConditionsYield
With 1H-imidazole In dichloromethane at 20℃; for 4h;100%
With 1H-imidazole In N,N-dimethyl-formamide for 24h; Ambient temperature;99%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃;99%
(R)-5-hydroxymethylpyrrolidin-2-one
66673-40-3

(R)-5-hydroxymethylpyrrolidin-2-one

methyl 3'-(cyanocarbonyl)-2,2'-binaphthalene-3-carboxylate
386707-15-9

methyl 3'-(cyanocarbonyl)-2,2'-binaphthalene-3-carboxylate

C28H23NO5

C28H23NO5

Conditions
ConditionsYield
With dmap In acetonitrile at 14℃; for 1.5h;100%
(R)-5-hydroxymethylpyrrolidin-2-one
66673-40-3

(R)-5-hydroxymethylpyrrolidin-2-one

2,2-dimethoxy-propane
77-76-9

2,2-dimethoxy-propane

(7aR)-3,3-dimethyltetrahydro-5H-pyrrolo[1,2-c][1,3]oxazol-5-one

(7aR)-3,3-dimethyltetrahydro-5H-pyrrolo[1,2-c][1,3]oxazol-5-one

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene for 1.5h; Dean-Stark; Reflux;100%
With camphor-10-sulfonic acid at 75℃; for 20h; Reagent/catalyst; Temperature; Time; Concentration;78%
With camphor-10-sulfonic acid at 75℃; for 20h; Time; Temperature; Reflux;78%
(R)-5-hydroxymethylpyrrolidin-2-one
66673-40-3

(R)-5-hydroxymethylpyrrolidin-2-one

ethyl vinyl ether
109-92-2

ethyl vinyl ether

(5R)-5-((tert-ethoxyethoxy)methyl)pyrrolidin-2-one
67040-46-4

(5R)-5-((tert-ethoxyethoxy)methyl)pyrrolidin-2-one

Conditions
ConditionsYield
With trichloroacetic acid In chloroform for 4h; Ambient temperature;97%
With trichloroacetic acid In dichloromethane at 20℃; for 16h;37%
With trichloroacetic acid In dichloromethane at 20℃; for 16h;37%
With trichloroacetic acid In dichloromethane at 20℃; for 16h;37%
With trichlorosilane; acetic acid In dichloromethane at 20℃; for 16h;37%
(R)-5-hydroxymethylpyrrolidin-2-one
66673-40-3

(R)-5-hydroxymethylpyrrolidin-2-one

D-pyrrolidone-5-carboxylic acid
4042-36-8

D-pyrrolidone-5-carboxylic acid

Conditions
ConditionsYield
With oxygen; sodium hydrogencarbonate; platinum In water for 4h; Ambient temperature;95%
(R)-5-hydroxymethylpyrrolidin-2-one
66673-40-3

(R)-5-hydroxymethylpyrrolidin-2-one

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

<(2R)-5-oxopyrrolidin-2-yl>methyl 4-methylbenzenesulfonate
128899-31-0

<(2R)-5-oxopyrrolidin-2-yl>methyl 4-methylbenzenesulfonate

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane at 20℃;95%
With dmap; triethylamine In dichloromethane at 0 - 23℃; for 12h; Inert atmosphere;93%
With dmap; triethylamine In dichloromethane at 20℃; for 18h; Cooling with ice;81%
(R)-5-hydroxymethylpyrrolidin-2-one
66673-40-3

(R)-5-hydroxymethylpyrrolidin-2-one

tert-butylchlorodiphenylsilane
58479-61-1

tert-butylchlorodiphenylsilane

(R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-pyrrolidin-2-one
138629-44-4

(R)-5-(tert-butyl-diphenyl-silanyloxymethyl)-pyrrolidin-2-one

Conditions
ConditionsYield
With 1H-imidazole In N,N-dimethyl-formamide for 12h; Ambient temperature;95%
With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 5h;95%
With dmap; triethylamine In dichloromethane88%
(R)-5-hydroxymethylpyrrolidin-2-one
66673-40-3

(R)-5-hydroxymethylpyrrolidin-2-one

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

<(2R)-5-oxopyrrolidin-2-yl>methyl methanesulfonate
128811-47-2

<(2R)-5-oxopyrrolidin-2-yl>methyl methanesulfonate

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0℃; for 1.5h;93%
With triethylamine In dichloromethane85%
With triethylamine In chloroform at 0 - 20℃;70%
With pyridine at 25℃; for 1.5h;60%
C17H33IOSi
925444-75-3

C17H33IOSi

(R)-5-hydroxymethylpyrrolidin-2-one
66673-40-3

(R)-5-hydroxymethylpyrrolidin-2-one

C22H41NO3Si
1084897-41-5

C22H41NO3Si

Conditions
ConditionsYield
With potassium carbonate; copper(l) iodide; N,N`-dimethylethylenediamine In acetonitrile for 18h; Heating / reflux;93%
triisopropylsilyl chloride
13154-24-0

triisopropylsilyl chloride

(R)-5-hydroxymethylpyrrolidin-2-one
66673-40-3

(R)-5-hydroxymethylpyrrolidin-2-one

(R)-5-Triisopropylsilanyloxymethyl-pyrrolidin-2-one

(R)-5-Triisopropylsilanyloxymethyl-pyrrolidin-2-one

Conditions
ConditionsYield
With 1H-imidazole In dichloromethane; N,N-dimethyl-formamide at 20℃; Inert atmosphere;88%
With 1H-imidazole In dichloromethane at 0 - 20℃; for 16h;37%
(R)-5-hydroxymethylpyrrolidin-2-one
66673-40-3

(R)-5-hydroxymethylpyrrolidin-2-one

Bromodiphenylmethane
776-74-9

Bromodiphenylmethane

(R)-5-(benzhydryloxymethyl)pyrrolidin-2-one

(R)-5-(benzhydryloxymethyl)pyrrolidin-2-one

Conditions
ConditionsYield
Stage #1: (R)-5-hydroxymethylpyrrolidin-2-one With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h; Inert atmosphere;
Stage #2: Bromodiphenylmethane In tetrahydrofuran; mineral oil at 50℃; for 12h;
88%
(R)-5-hydroxymethylpyrrolidin-2-one
66673-40-3

(R)-5-hydroxymethylpyrrolidin-2-one

(R)-5-(azidomethyl)-2-pyrrolidone
173828-76-7

(R)-5-(azidomethyl)-2-pyrrolidone

Conditions
ConditionsYield
With hydrogen azide; di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 1h;87%
With tris-(2-chloro-ethyl)-amine; triphenylphosphine; diethylazodicarboxylate
(R)-5-hydroxymethylpyrrolidin-2-one
66673-40-3

(R)-5-hydroxymethylpyrrolidin-2-one

benzaldehyde
100-52-7

benzaldehyde

(2S,5R)-2-phenyl-1-aza-3-oxabicyclo<3.3.0>octan-8-one
118918-76-6

(2S,5R)-2-phenyl-1-aza-3-oxabicyclo<3.3.0>octan-8-one

Conditions
ConditionsYield
With toluene-4-sulfonic acid In toluene Reflux; Dean-Stark;85%
With 4 A molecular sieve; toluene-4-sulfonic acid In toluene Heating;72%
With toluene-4-sulfonic acid Inert atmosphere;67%
With water; toluene-4-sulfonic acid In toluene at 20℃; Reflux;62%
With toluene-4-sulfonic acid In toluene for 16h; Reflux;52%
4-Bromo-2-methylphenol
2362-12-1

4-Bromo-2-methylphenol

(R)-5-hydroxymethylpyrrolidin-2-one
66673-40-3

(R)-5-hydroxymethylpyrrolidin-2-one

(R)-5-(4-Bromo-2-methylphenoxymethyl)-2-pyrrolidinone
215382-97-1

(R)-5-(4-Bromo-2-methylphenoxymethyl)-2-pyrrolidinone

Conditions
ConditionsYield
In ethyl acetate; SiO283%
(R)-5-hydroxymethylpyrrolidin-2-one
66673-40-3

(R)-5-hydroxymethylpyrrolidin-2-one

[1-(4-bromo-phenyl)-hexyloxy]-tert-butyl-dimethyl-silane
836643-56-2

[1-(4-bromo-phenyl)-hexyloxy]-tert-butyl-dimethyl-silane

C23H39NO3Si
1073241-71-0

C23H39NO3Si

Conditions
ConditionsYield
With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine In acetonitrile Heating / reflux;82%
Dimethoxymethane
109-87-5

Dimethoxymethane

(R)-5-hydroxymethylpyrrolidin-2-one
66673-40-3

(R)-5-hydroxymethylpyrrolidin-2-one

C7H13NO3
1365178-37-5

C7H13NO3

Conditions
ConditionsYield
With trifluorormethanesulfonic acid In dichloromethane at 20℃; for 6h; Inert atmosphere;80%
3-bromo-2-chloro-5-nitropyridine
5470-17-7

3-bromo-2-chloro-5-nitropyridine

(R)-5-hydroxymethylpyrrolidin-2-one
66673-40-3

(R)-5-hydroxymethylpyrrolidin-2-one

(R)-5-(((3-bromo-5-nitropyridin-2-yl)oxy)methyl)pyrrolidin-2-one

(R)-5-(((3-bromo-5-nitropyridin-2-yl)oxy)methyl)pyrrolidin-2-one

Conditions
ConditionsYield
With potassium carbonate In acetonitrile at 100℃; for 16h; Inert atmosphere;79%
(R)-5-hydroxymethylpyrrolidin-2-one
66673-40-3

(R)-5-hydroxymethylpyrrolidin-2-one

(5R)-5-(bromomethyl)pyrrolidin-2-one
98612-60-3

(5R)-5-(bromomethyl)pyrrolidin-2-one

Conditions
ConditionsYield
With carbon tetrabromide; triphenylphosphine In dichloromethane for 1.5h; Ambient temperature;77%
With carbon tetrabromide; triphenylphosphine In acetonitrile73%
With carbon tetrabromide; triphenylphosphine In acetonitrile at 0 - 20℃; for 24h;
1-iodo-4-(methoxymethoxy)benzene
98491-29-3

1-iodo-4-(methoxymethoxy)benzene

(R)-5-hydroxymethylpyrrolidin-2-one
66673-40-3

(R)-5-hydroxymethylpyrrolidin-2-one

(R)-5-Hydroxymethyl-1-(4-methoxymethoxy-phenyl)-pyrrolidin-2-one

(R)-5-Hydroxymethyl-1-(4-methoxymethoxy-phenyl)-pyrrolidin-2-one

Conditions
ConditionsYield
With copper(l) iodide; caesium carbonate; N,N`-dimethylethylenediamine In N,N-dimethyl-formamide Heating;71%
3-methoxy-4-[2-(1-pyrrolidinyl)ethoxy]phenyl 2-(4-hydroxyphenyl)benzo[b]thiophen-3-yl ketone
215388-44-6

3-methoxy-4-[2-(1-pyrrolidinyl)ethoxy]phenyl 2-(4-hydroxyphenyl)benzo[b]thiophen-3-yl ketone

(R)-5-hydroxymethylpyrrolidin-2-one
66673-40-3

(R)-5-hydroxymethylpyrrolidin-2-one

3-Methoxy-4-[2-(1-pyrrolidinyl)ethoxy]phenyl (R)-2-[4-(5-Oxopyrrolidin-2-ylmethoxy)phenyl]benzo[b]thiophen-3-yl Ketone
215387-32-9

3-Methoxy-4-[2-(1-pyrrolidinyl)ethoxy]phenyl (R)-2-[4-(5-Oxopyrrolidin-2-ylmethoxy)phenyl]benzo[b]thiophen-3-yl Ketone

Conditions
ConditionsYield
With triethanolamine In tetrahydrofuran; SiO270%
2-(4-bromophenyl)-1,3-thiazole
27149-27-5

2-(4-bromophenyl)-1,3-thiazole

(R)-5-hydroxymethylpyrrolidin-2-one
66673-40-3

(R)-5-hydroxymethylpyrrolidin-2-one

C14H14N2O2S
1073242-22-4

C14H14N2O2S

Conditions
ConditionsYield
With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine In acetonitrile for 18h; Heating / reflux;67%
C14H29IOSi
63358-20-3

C14H29IOSi

(R)-5-hydroxymethylpyrrolidin-2-one
66673-40-3

(R)-5-hydroxymethylpyrrolidin-2-one

C19H37NO3Si
1084897-20-0

C19H37NO3Si

Conditions
ConditionsYield
With potassium carbonate; copper(l) iodide; N,N`-dimethylethylenediamine In acetonitrile for 18h; Heating / reflux;67%
(R)-5-hydroxymethylpyrrolidin-2-one
66673-40-3

(R)-5-hydroxymethylpyrrolidin-2-one

(R)-(+)-5-(chloromethyl)-2-pyrrolidone
138541-53-4

(R)-(+)-5-(chloromethyl)-2-pyrrolidone

Conditions
ConditionsYield
With methanesulfonyl chloride In N,N-dimethyl-formamide at 65℃; for 16h;65%
1-bromo-4-n-hexylbenzene
23703-22-2

1-bromo-4-n-hexylbenzene

(R)-5-hydroxymethylpyrrolidin-2-one
66673-40-3

(R)-5-hydroxymethylpyrrolidin-2-one

C17H25NO2
1043876-44-3

C17H25NO2

Conditions
ConditionsYield
With copper(l) iodide; potassium carbonate; N,N`-dimethylethylenediamine In acetonitrile for 72h; Heating/reflux;63%
With potassium carbonate; copper(l) iodide; N,N`-dimethylethylenediamine In acetonitrile for 72h; Reflux;63%
para-chlorotoluene
106-43-4

para-chlorotoluene

(R)-5-hydroxymethylpyrrolidin-2-one
66673-40-3

(R)-5-hydroxymethylpyrrolidin-2-one

(R)-5-(hydroxymethyl)-1-(p-tolyl)pyrrolidin-2-one

(R)-5-(hydroxymethyl)-1-(p-tolyl)pyrrolidin-2-one

Conditions
ConditionsYield
With copper(I) oxide; potassium phosphate; N1,N2-bis(thiophen-2-ylmethyl)oxalamide In tert-butyl alcohol at 130℃; for 24h; Schlenk technique;58%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

(R)-5-hydroxymethylpyrrolidin-2-one
66673-40-3

(R)-5-hydroxymethylpyrrolidin-2-one

tert-butylchlorodiphenylsilane
58479-61-1

tert-butylchlorodiphenylsilane

trimethyl orthoformate
149-73-5

trimethyl orthoformate

(5R)-1-(tert-butoxycarbonyl)-2-methoxy-5-(tert-butyldiphenylsilanyloxymethyl)pyrrolidine
203301-82-0

(5R)-1-(tert-butoxycarbonyl)-2-methoxy-5-(tert-butyldiphenylsilanyloxymethyl)pyrrolidine

Conditions
ConditionsYield
Multistep reaction.;52%
6-benzyloxy-2-(4-hydroxyphenyl)-3-[3-methoxy-4-[(1-pyrrolidinyl)methyl]benzyl]benzo[b]thiophene
193966-79-9

6-benzyloxy-2-(4-hydroxyphenyl)-3-[3-methoxy-4-[(1-pyrrolidinyl)methyl]benzyl]benzo[b]thiophene

(R)-5-hydroxymethylpyrrolidin-2-one
66673-40-3

(R)-5-hydroxymethylpyrrolidin-2-one

(R)-6-Benzyloxy-3-[3-methoxy-4-(1-pyrrolidinylmethyl)benzyl]-2-[4-(5-oxopyrrolidin-2-ylmethoxy)phenyl]benzo[b]thiophene
215388-70-8

(R)-6-Benzyloxy-3-[3-methoxy-4-(1-pyrrolidinylmethyl)benzyl]-2-[4-(5-oxopyrrolidin-2-ylmethoxy)phenyl]benzo[b]thiophene

Conditions
ConditionsYield
50%

66673-40-3Relevant academic research and scientific papers

HETEROARYL(HETEROCYCLYL)METHANOL COMPOUNDS USEFUL IN THE TREATMENT OF HYPERGLYCAEMIA

-

Page/Page column 53, (2020/10/09)

There is herein provided a compound of formula I (I) or a pharmaceutically acceptable salt thereof, wherein the ring comprising Q1 to Q5, R1, m, X1 and ring A have meanings as provided in the description.

HETEROCYCLYL(PHENYL)METHANOL COMPOUNDS USEFUL IN THE TREATMENT OF HYPERGLYCAEMIA

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Page/Page column 53, (2020/10/09)

There is herein provided a compound of formula I or a pharmaceutically acceptable salt thereof, wherein X, R1, R2, R3, ring A, n and y have meanings as provided in the description.

INHIBITORS OF APOL1 AND METHODS OF USING SAME

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Paragraph 00312, (2020/07/14)

The disclosure provides at least one entity chosen from compounds of formula (I), solid state forms of the same, compositions comprising the same, and methods of using the same, including use in treating focal segmental glomerulosclerosis (FSGS) and/or non-diabetic kidney disease (NDKD).

LACTAM COMPOUNDS AS EP4 RECEPTOR-SELECTIVE AGONISTS FOR USE IN THE TREATMENT OF EP4-MEDIATED DISEASES AND CONDITIONS

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, (2016/05/02)

Disclosed herein are compounds of formula (I) wherein L1, L2, L3, L4, R1, R4, R5, R6, and s are as defined in the specification. Compounds of formula (I) are EP4 agonists useful in the treatment of glaucoma, osteoporosis, bone fracture, periodontal bone loss, orthopedic implant, alopecia, neuropathic pain, and related disorders. Pharmaceutical compositions and methods of treating conditions or disorders are also described.

NOVEL INDOLE DERIVATIVES AND THEIR USE IN NEURODEGENERATIVE DISEASES

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, (2016/11/24)

The present invention relates to indole compounds, and pharmaceutically acceptable compositions thereof, useful as antagonists of P2X7, and for the treatment of P2X7-related disorders.

Chiral-Substituted Poly-N-vinylpyrrolidinones and Bimetallic Nanoclusters in Catalytic Asymmetric Oxidation Reactions

Hao, Bo,Gunaratna, Medha J.,Zhang, Man,Weerasekara, Sahani,Seiwald, Sarah N.,Nguyen, Vu T.,Meier, Alex,Hua, Duy H.

supporting information, p. 16839 - 16848 (2017/01/10)

A new class of poly-N-vinylpyrrolidinones containing an asymmetric center at C5 of the pyrrolidinone ring were synthesized from l-amino acids. The polymers, particularly 17, were used to stabilize nanoclusters such as Pd/Au for the catalytic asymmetric oxidations of 1,3- and 1,2-cycloalkanediols and alkenes, and Cu/Au was used for C-H oxidation of cycloalkanes. It was found that the bulkier the C5 substituent in the pyrrolidinone ring, the greater the optical yields produced. Both oxidative kinetic resolution of (±)-1,3- and 1,2-trans-cycloalkanediols and desymmetrization of meso cis-diols took place with 0.15 mol % Pd/Au (3:1)-17 under oxygen atmosphere in water to give excellent chemical and optical yields of (S)-hydroxy ketones. Various alkenes were oxidized with 0.5 mol % Pd/Au (3:1)-17 under 30 psi of oxygen in water to give the dihydroxylated products in >93% ee. Oxidation of (R)-limonene at 25 °C occurred at the C-1,2-cyclic alkene function yielding (1S,2R,4R)-dihydroxylimonene 49 in 92% yield. Importantly, cycloalkanes were oxidized with 1 mol % Cu/Au (3:1)-17 and 30% H2O2 in acetonitrile to afford chiral ketones in very good to excellent chemical and optical yields. Alkene function was not oxidized under the reaction conditions. Mechanisms were proposed for the oxidation reactions, and observed stereo- and regio-chemistry were summarized.

METHODS, SYSTEMS, AND COMPOSITIONS FOR PROMOTING BONE GROWTH

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, (2015/02/02)

The present invention relates to novel bone compositions for locally delivering a therapeutic agent to the site of a bone defect. Therapeutic agents may promote repair of the bone defect and/or treat conditions or disorders such as pain, inflammation, cancer, and infection. The compositions include calcium phosphate cements and a demineralized bone matrix or a collagen sponge. The compositions are useful for implantation in a patient at the site of a bone defect.

CARBONITRILE DERIVATIVES AS SELECTIVE ANDROGEN RECEPTOR MODULATORS

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, (2015/12/17)

The present invention relates to a compound of Formula 1, 2 or 3: I II III wherein A is N or -CR0--, where R0 is hydrogen, C1-C6 linear or branched chain alkyl, etc., Z is -CRe --, or, -N--, where Re is hydrogen, C1 -C6 linear or branched chain alkyl, etc.; R1 is hydrogen, C1 -C6 linear or branched chain alkyl, etc.; R2 are independently hydrogen or C1-C6 linear or branched chain alkyl; R3 and R4 are independently hydrogen, C1C6 linear or branched chain alkyl, etc.;. R5 and R6 are independently hydrogen or C1-C6 linear or branched chain alkyl, etc.; R8 is hydrogen, C1 -C6 linear or branched chain alkyl, etc.; R9 and R10 are independently hydrogen or C1- C6 linear or branched chain alkyl, etc.; Q is --CO--, --(CH2)q--, --(CHRs)q--, or -(CRsRt)q- -, where Rs and Rt are independently C1-C6 linear or branched chain alkyl, aryl, alkylaryl, heteroaryl or alkylheteroaryl; where q is 0, 1, 2, or 3; and, where n is 0, 1, 2, 3, 4 or 5; or, a pharmaceutically acceptable salt thereof, for the treatment of certain diseases, particularly those affected or mediated by the androgen receptor; to compbinations comprising such compounds with a second pharmaceutically active ingredient; to compositions containing such combinations; and to such combinations for the treatment of various diseases, particularly, those affected or mediated by the androgen receptor.

LACTAM COMPOUNDS AS EP4 RECEPTOR-SELECTIVE AGONISTS FOR USE IN THE TREATMENT OF EP4-MEDIATED DISEASES AND CONDITIONS

-

, (2016/10/09)

Disclosed herein are compounds of formula (I) wherein L 1 , L 2 , L 3 , L 4 , R 1 , R 4 , R 5 , R 6 , and s are as defined in the specification. Compounds of formula (I) are EP 4 agonists useful in the treatment of glaucoma, osteoporosis, bone fracture, periodontal bone loss, orthopedic implant, alopecia, neuropathic pain, and related disorders. Pharmaceutical compositions and methods of treating conditions or disorders are also described.

DIFLUOROLACTAM COMPOSITIONS FOR EP4-MEDIATED OSTEO RELATED DISEASES AND CONDITIONS

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, (2014/02/15)

Disclosed herein are compositions and methods of treating osteroporosis, bone fracture, bone loss, and increasing bone density by administration of compounds of formula (I) or compositions comprising a compound of formula (I) and a pharmaceutically acceptable carrier, wherein L1, L2, L4, R1, R4, R5, R6, and s are as defined in the specification.

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