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116539-57-2

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Basic Information

Molecular Structure:
CAS No.:	116539-57-2
Name:	(R)-(+)-3-(N-METHYLAMINO)-1-(2-THIENYL)-1-PROPANOL
Article Data:	18

Formula:	C8H13NOS
Molecular Weight:	171.263
Synonyms:	(R)-(+)-3-(N-METHYLAMINO)-1-(2-THIENYL)-1-PROPANOL;(1R)-3-(Methylamino)-1-(2-thienyl)-1-propanol;(R)-3-Methylamino-1-(2-thienyl)-1-propanol;N-Methyl[(R)-3-hydroxy-3-(2-thienyl)propyl]amine;(R)-3-(Methylamino)-1-(thiophen-2-yl)propan-1-ol
EINECS:	171.26
Density:	1.128
Boiling Point:	294.3±35.0 °C(Predicted)
PSA:	60.50000
LogP:	1.78190

Synthetic route

: N-methyl-3-(thien-2-yl)-3-morpholino-propylamine hydrochloride

: 116539-57-2
(R)-3-(methylamino)-1-(thiophen-2-yl)propan-1-ol

Conditions	Yield
With hydrogen; potassium carbonate; [Rh{(RC,SP)-duanphos}(norbornadiene)]SbF6 In methanol at 20℃; under 7500.6 Torr; for 12h;	93%

: 597581-30-1
(R)-(3-hydroxy-3-thiophen-2-yl-propyl)carbamic acid ethyl ester

: 116539-57-2
(R)-3-(methylamino)-1-(thiophen-2-yl)propan-1-ol

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran for 1.5h; Heating;	88%
With lithium aluminium tetrahydride In tetrahydrofuran for 14h; Reflux;	87%
With lithium aluminium tetrahydride In tetrahydrofuran for 2h; Heating;

: N-methyl-3-(thien-2-yl)-3-morpholino-propylamine hydrochloride

A: 116539-55-0
(S)-3-methylamino-1-(2-thienyl)-1-propanol

B: 116539-57-2
(R)-3-(methylamino)-1-(thiophen-2-yl)propan-1-ol

Conditions	Yield
With lithium aluminium tetrahydride Product distribution / selectivity;	A 74% B n/a
With hydrogen; sodium methylate; bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; (S)-(-)-(6,6’-dimethoxybiphenyl-2,2’-diyl)bis(diphenylphosphine) In methanol at 30 - 50℃; under 22502.3 Torr; for 24h; Product distribution / selectivity;	A 12.7 - 20.4 %Chromat. B n/a
With hydrogen; sodium methylate; ethyl acetoacetate; [(12aS)-6,7-dihudrodibenzo[e,g][1,4]dioxocin-1,12-diyl]bis[diphenylphosphine]; bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate In methanol at 50℃; under 22502.3 Torr; for 24h; Product distribution / selectivity;	A 6.2 %Chromat. B n/a
With hydrogen; [(12aS)-6,7-dihudrodibenzo[e,g][1,4]dioxocin-1,12-diyl]bis[diphenylphosphine]; [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2 In methanol at 50℃; under 22502.3 Torr; for 24h; Product distribution / selectivity;	A 11.6 %Chromat. B n/a
With hydrogen; [(12aS)-6,7-dihudrodibenzo[e,g][1,4]dioxocin-1,12-diyl]bis[diphenylphosphine]; bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate In methanol at 50℃; under 22502.3 Torr; for 24h; Product distribution / selectivity;	A 4 %Chromat. B n/a

: 164071-55-0
(R)-3-chloro-1-thiophenyl-2-yl-propan-1-ol

: 74-89-5
methylamine

: 116539-57-2
(R)-3-(methylamino)-1-(thiophen-2-yl)propan-1-ol

Conditions	Yield
In ethanol at 90℃; Sealed tube;	62%
In ethanol; water at 130℃; for 1h; Sealed tube;	55%
In ethanol at 90℃; Sealed tube;	41%
In ethanol at 90℃; Sealed tube;	41%

: N-methyl-3-(thien-2-yl)-3-morpholino-propylamine hydrochloride

: 7480-35-5, 13286-59-4, 74165-73-4, 126456-43-7, 136030-00-7, 140632-19-5, 140632-20-8
(1S,2R)-1-amino-2-indanol

A: 116539-55-0
(S)-3-methylamino-1-(2-thienyl)-1-propanol

B: 116539-57-2
(R)-3-(methylamino)-1-(thiophen-2-yl)propan-1-ol

Conditions	Yield
With sodium hydroxide; (p-cymene)-ruthenium(II) chloride dimer In isopropyl alcohol at 20 - 85℃; for 5h;	A 39% B n/a

: 116539-56-1
3-(methylamino)-1-(thiophen-2-yl)propan-1-ol

A: 116539-55-0
(S)-3-methylamino-1-(2-thienyl)-1-propanol

B: 116539-57-2
(R)-3-(methylamino)-1-(thiophen-2-yl)propan-1-ol

Conditions	Yield
With (S)-Mandelic acid In water at 29 - 50℃;	A 27% B n/a
With diethylamine In ethanol; n-heptane Resolution of racemate;

: 919530-16-8
(2R,6R)-2-[(S)-1-triisopropylsilyloxyethyl]-3-methyl-6-(thiophen-2-yl)-1,3-oxazinane

: 116539-57-2
(R)-3-(methylamino)-1-(thiophen-2-yl)propan-1-ol

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; water at 20℃; for 4h;

: 919530-11-3
(2R,6R)-2-[(S)-1-triisopropylsilyloxyethyl]-6-(thiophen-2-yl)-[1,3]oxazinan-4-one

: 116539-57-2
(R)-3-(methylamino)-1-(thiophen-2-yl)propan-1-ol

Conditions	Yield
Multi-step reaction with 3 steps 1: LiHMDS / tetrahydrofuran / 0 - 20 °C 2: Ph2SiH2 / RhH(CO)(PPh3)3 / tetrahydrofuran / 15 h / 20 °C 3: HCl / H2O; tetrahydrofuran / 4 h / 20 °C View Scheme

: 919530-13-5
(2R,6R)-N-methyl-2-[(S)-1-triisopropylsilyloxyethyl]-6-(thiophen-2-yl)-[1,3]oxazinan-4-one

: 116539-57-2
(R)-3-(methylamino)-1-(thiophen-2-yl)propan-1-ol

Conditions	Yield
Multi-step reaction with 2 steps 1: Ph2SiH2 / RhH(CO)(PPh3)3 / tetrahydrofuran / 15 h / 20 °C 2: HCl / H2O; tetrahydrofuran / 4 h / 20 °C View Scheme

: 98-03-3
thiophene-2-carbaldehyde

polymer-bound-N-(3-(4-bromophenyl)-3-oxopropanamide): polymer-bound-N-(3-(4-bromophenyl)-3-oxopropanamide)

: 116539-57-2
(R)-3-(methylamino)-1-(thiophen-2-yl)propan-1-ol

Conditions	Yield
Multi-step reaction with 5 steps 1: 54 percent / BF3*Et2O / CH2Cl2 / -78 - 20 °C 2: aluminum amalgam / propan-2-ol 3: LiHMDS / tetrahydrofuran / 0 - 20 °C 4: Ph2SiH2 / RhH(CO)(PPh3)3 / tetrahydrofuran / 15 h / 20 °C 5: HCl / H2O; tetrahydrofuran / 4 h / 20 °C View Scheme

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