A facile, high yield synthesis of γ- and δ-hydroxyamides

Article abstract of DOI:10.1081/SCC-100105114

γ- and δ-Hydroxyamides can be prepared in high yields by heating a lactone with ammonia in a pressure tube. The ammonia can be removed by controlled evaporation with ice/acetone cooling.

Full text of DOI:10.1081/SCC-100105114

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A FACILE, HIGH YIELD SYNTHESIS OF γ- AND δ-
HYDROXYAMIDES
Stephen K. Taylor a , Nathan D. Ide a , Michael E. Silver a & Mari L. Stephan a
a Department of Chemistry , Hope College , Holland, Michigan, 49422, U.S.A.
Published online: 09 Nov 2006.
To cite this article: Stephen K. Taylor , Nathan D. Ide , Michael E. Silver & Mari L. Stephan (2001) A FACILE, HIGH YIELD
SYNTHESIS OF γ- AND δ-HYDROXYAMIDES, Synthetic Communications: An International Journal for Rapid Communication of
Synthetic Organic Chemistry, 31:16, 2391-2397, DOI: 10.1081/SCC-100105114
To link to this article: http://dx.doi.org/10.1081/SCC-100105114
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SYNTHETIC COMMUNICATIONS, 31(16), 2391–2397 (2001)
A FACILE, HIGH YIELD SYNTHESIS OF
c- AND d-HYDROXYAMIDES
Stephen K. Taylor,* Nathan D. Ide,
Michael E. Silver, andMari L. Stephan
Department of Chemistry, Hope College,
Holland, Michigan 49422
ABSTRACT
g- and d-Hydroxyamides can be prepared in high yields by
heating a lactone with ammonia in a pressure tube.The
ammonia can be removed by controlled evaporation with
ice/acetone cooling.
We needed a series of racemic g-hydroxyamides 2a–d and k (eq 1 and
Table 1) for biotransformation studies.1 However, a review of the literature
strongly indicated that a straightforward, general method for the prepara-
tion of these types of compounds was needed.2
(1)
Hydroxyamides have been synthesized recently by treating a g-lactone
with methylaluminumchloroamide (prepared from trimethyl aluminum and
*Corresponding author.
2391
Copyright & 2001 by Marcel Dekker, Inc.
www.dekker.com

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2392
TAYLOR ET AL.
NH4Cl).3 We found this method to work nicely but only in only approxi-
mately 50% yield4 (e.g. 1b to 2b, Table 1).This method is probably based on
a popular, reliable preparation of amides from esters5 utilizing the same or
similar reagents.6–8
In looking at the difference between 1 and 2 (R0 ¼ H), we reasoned that
the only difference was NH3.Reported methods using NH equivalents
3
include reacting a lactone with conc.NH 4OH,9 conc.NH 4OH/EtOH,10
NH4OH/NH4Cl,11 NH3 at 50ꢀC12 or elevated temperatures (120ꢀC),2b or
simple amines,13–15 but they can be described as inconsistent in the con-
ditions used.15 We don’t favor the use of aqueous or ethanolic NH4OH
for hydroxyamide preparation from g-lactones because in limited studies,
we only achieved low yields of hydroxyamide products.We also note that in
some cases where these methods were used, no yields were reported.9,10
The following method gave consistently high yields of the desired
hydroxyamide products from a variety of lactone substrates via a simple,
direct procedure.We sealed lactones in a pressure tube with NH and
3
warmed them for about a week at 50–60ꢀC, opened the tube and allowed
the ammonia to evaporate slowly with ice/acetone cooling (ꢁ ꢂ 20ꢀC).
Excellent, white crystalline 4- and 5-hydroxyamide products were obtained
in high yields from five- and six-membered ring lactones.Recrystallization
from ethyl acetate produced very pure crystals that gave excellent analytical
results. Table 1 lists the compounds investigated.All lactone precursors
were commercially available.The yields were typically ꢃ 90% for g- and
d-lactones and both were treated similarly, even though d-lactones react
slower.15 This caused no problem, and it showed the generality of the reaction
procedures.
Table 1. Hydroxyamide Preparations
Entry
Lactone
n¼
R¼
R0¼
Hydroxyamide
Yield %
1
2
3
4
5
6
7
8
9
1a
1b
1c
1d
1e
1f
1g
1h
1i
1
1
1
1
1
1
1
1
2
2
2
–CH2CH3
–(CH2)3CH3
–(CH2)4CH3
–(CH2)7CH3
Ph–
–(CH2)3CH3
–(CH2)4CH3
–(CH2)4CH3
–(CH2)4CH3
–(CH2)5CH3
–(CH2)6CH3
H
H
H
H
2a
2b
2c
2d
2e
2f
2g
2h
2i
87
92
94
99
92
81
89
98
69
90
89
H
CH3
CH3
–CH2CH3
H
10
11
1j
1k
H
H
2j
2k

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c- AND d-HYDROXYAMIDES
2393
General methods to make g-hydroxynitriles are available,16 and
numerous attempts were made to partially hydrolyze the g-hydroxynitriles
17
to g-hydroxyamides, but only low yields were achieved.Typical methods
using H2O2/NaOH led to lactones.KF/alumina
18
nicely did the partial
hydrolysis, but we only got a 20% yield, and liquid chromatography was
necessary to separate the reactants and products.This method was aban-
doned in favor of the procedure described herein.
EXPERIMENTAL
All racemic lactones were commercially available.The NH
used was
3
reagent grade anhydrous ammonia.All proton NMR spectra were per-
formed on a 400 MHz spectrometer, and carbon-13 spectra were done (at
100.6 MHz) with high signal/noise ratio to prove product purities: C, H
analyses were also done to prove product purities.Mass spectral analyses
led to ambiguous fragmentations, and are not included.
The vacuum and high pressure procedures (sealed tubes) should be done
behind a safety shield!
General Procedure for c- and d-Hydroxyamide
Preparations from Lactones
4-Hydroxyhexanamide (2a). A vacuum (10ꢂ2 torr) was applied to a
thick-walled 100 mL reaction tube containing 1.02 g (8.9 mmol) g-caprolac-
tone that was cooled with liquid N2.Approximately 20 mL of NH was
3
condensed into the tube via a glass T.The tube was then sealed off with a
flame and was allowed to warm to room temperature and sit for 10 days.
The tube was then cooled with liquid N2 and opened, and the ammonia was
allowed to evaporate slowly at room temperature (sometimes this evapora-
tion method led to bumping and the loss of some product).After evapora-
tion, the tube contained white solid, which was dissolved and rinsed out with
a total of approximately 7 mL of hot EtOAc.Upon cooling, white crystals
of 4-hydroxyhexanamide were isolated (0.95 g). From the filtrate, an addi-
tional 0.065 g were obtained, 1.015 g (87%), mp 76–77.5ꢀC (lit.19 74ꢀC).A
1.00 g sample of g-caprolactone was sealed in a tube similarly, only this time
it was warmed to 50ꢀC for 6 days and then opened after cooling with liquid
N2.The NH was allowed to evaporate with ice/acetone cooling applied to
3
the tube.This cooling method allowed a very controlled evaporation of the
NH3, prevented bumping, and was the preferred procedure.A total of
0.986 g (86%) of solid, mp 76–77.5ꢀC, was obtained from the combined

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2394
TAYLOR ET AL.
crystallizations.A tube sealed and warmed similarly for two days still had
unreacted lactone in it.IR (mineral oil) 3700–3000, 1674 (C ¼O), 1616, 1471,
1
1121, 938 cmꢂ1. H NMR (d6 DMSO) d 7.25 (s, 1H), 6.7 (s, 1H), 4.4 (d,
J ¼ 5.4 Hz, OH), 3.3 (m, 1H), 2.2 (m, 2H), 1.6-1.2 (m, 4H), 0.85 (t, J ¼ 7.5 Hz,
3H). 13C NMR (d6 DMSO) d 175 (C¼O), 71.4, 33.1, 32.4, 30.5, 10.8. Anal
Calcd for C6H13NO2: C, 54.94; H, 9.99. Found C, 54.83, H, 10.03.
4-Hydroxyoctanamide (2b). g-Octanoic lactone (1.66 g, 11.2 mmol) was
sealed in a thick-walled reaction tube with 22 mL of NH3 as above, and the
solution was warmed to 50ꢀC for 6 days.Opening the tube at liquid N
2
temperature and evaporating the NH3 off with ice/acetone cooling led to
1.682 g of white crystals, and the filtrate yielded 25 mg more 2b (total 1.707 g,
91.7%), mp 84–86ꢀC (lit.2a 84–84.5ꢀC).IR (mineral oil) 3400–3160, 1680
1
(C¼O), 1600, 1456, 1080 cmꢂ1. H NMR (d6 DMSO) d 7.25 (s, 1H), 6.7
(s, 1H), 4.4 (d, J ¼ 5.1 Hz, 1H), 3.4 (m, 1H), 2.2–2.0 (m, 2H), 1.6 (m, 1H), 1.5
(m, 1H), 1.2-1.4 (m, 6H), 0.86 (t, J ¼ 7 Hz, 3H). 13C NMR (d6 DMSO)
d 176.1, 70.8, 38.5, 34.5, 33.3, 29.22, 24.0, 15.8. Anal Calcd for C8H17NO2:
C, 60.35; H, 10.76. Found C, 60.44; H, 10.97.
4-Hydroxynonanamide (2c). g-Nonanoic lactone (0.945 g, 6 mmol) was
combined with 20 mL ammonia and heated as above at 50–60ꢀC for 7 days.
Evaporation with ice/acetone cooling led to 0.987 g 2c (94%), mp 82–84ꢀC
(lit.2a 85–86ꢀC).IR (mineral oil) 3500–3100, 1680 (C ¼O), 1603, 1458 cmꢂ1
.
1H NMR (CDCl3) d 5.7 (s, 1H), 5.5 (s, 1H), 3.6 (m, 1H), 2.5 (d, J ¼ 5 Hz,
1H), 2.4 (t of d, J ¼ 6.5 and 1.5 Hz, 2H), 1.9–1.8 (m, 1H), 1.62–1.71 (m, 2H),
1.5–1.2 (m, 7H), 0.87 (t, J ¼ 6.9 Hz, 3H). 13C NMR (d6 DMSO) d 180.8,
75.6, 43.5, 39.3, 38.1, 37.9, 31.4, 28.6, 20.4. Anal Calcd for C9H19NO2: C,
62.39; H, 11.05. Found C, 62.33; H, 11.23.
4-Hydroxydodecanamide (2d). g-Dodecanoic lactone (1.44 g,
7.26 mmol) was sealed with 20 ml of NH3 and warmed to 50ꢀC for 7 days.
A total of 1.54 g (99%) of 2d was obtained, mp 103–105ꢀC (lit.20 105ꢀC).IR
1
(mineral oil) 3500–3100 (2 bands), 1682, 1605, 1456, 1093 cmꢂ1. H NMR
(d6 DMSO) d 7.2 (s, 1H), 6.7 (s, 1H), 4.38 (d, J ¼ 5 Hz, 1H), 3.4 (m, 1H), 2.1
(m, 2H), 1.5 (m, 1H), 1.4 (m, 1H), 1.4–1.2 (m, 14H), 0.86 (t, J ¼ 7 Hz, 3H).
13C NMR (d6 DMSO) d 176.1, 70,9, 38.8, 34.5, 33.3, 33.0, 30.9, 30.8, 30.4,
27.0, 23.8, 15.7. Anal Calcd for C12H25NO2: C, 66.94; H, 11.70. Found C,
66.92; H, 11.76.
4-Phenyl-4-hydroxybutanamide (2e). g-Phenyl-g-butyrolactone (1.29 g,
7.95 mmol) was sealed with 20 ml of NH3 for 3 days at 50ꢀC (the reaction
solution began to turn brown and was stopped: The color was removed with
decolorizing charcoal).A total of 13.9 g of
2e was obtained (97%),
mp 80–82ꢀC (lit.21 84–85ꢀC).IR (mineral oil) 3500–3090, 1683 (C ¼O),
1
1614, 1452, 1444, 1089 cmꢂ1. H NMR (d6 DMSO) d 7.31 (s, 2H), 7.29
(s, 2H), 7.28 (s, NH), 7.2 (m, 1H), 6.74 (s, NH), 5.28 (d, J ¼ 3.2 Hz, OH),

ORDER
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c- AND d-HYDROXYAMIDES
2395
4.5 (q, J ¼ 5.2 Hz, 1H), 2.1 (t, J ¼ 7 Hz, 2H), 1.8 (q, J ¼ 6.8 Hz, 2H). 13C NMR
(d6 DMSO) d 175.1, 146.7, 128.6 (2C), 127.3, 126.4 (2C), 72.5, 35.7, 32.3.
Anal Calcd for C10H13NO2: C, 67.02; H, 7.31. Found C, 67.26; H, 7.26.
N-Methyl-4-hydroxyoctanamide (2f ). g-Octanoic lactone (1.45 g,
10 mmol) was placed in an Ace Pressure tube with 20 mL of 2M CH3NH2
in THF and the solution was warmed to 50ꢀC for 24 hours.It was cooled to
room temperature, and the liquid was allowed to evaporate overnight.The
solid was recrystallized from EtOAc/hexane (7 mL of 5:2 EtOAc:hexane),
giving 1.434 g of hydroxyamide 2f (81%), mp 51–53ꢀC.IR (mineral oil)
3600–3000, 1653 (C¼O), 1564, 1412, 1049 cmꢂ1
.
1H NMR (d6 DMSO)
d 6.4 (s, 1H), 3.68 (s, 1H), 3.55 (m, 1H), 2.7 (d, J ¼ 4.7 Hz, 3H), 2.3 (m,
2H), 1.7 (m, 2H), 1.35 (m, 6H), 0.85 (t, J ¼ 7.1 Hz, 3H). 13C NMR (d6
DMSO) d 173.6 (C¼O), 70, 37.6, 33.8, 32.7, 28.3, 26.2, 23.1, 14.8. Anal
Calcd for C9H19NO2: C, 62.39; H, 11.05. Found C, 62.41, H, 10.94.
N-Methyl-4-hydroxynonanamide (2g). g-Nonanoic lactone (1.0 g,
6.4 mmol) was combined with 20 mL of 2M CH3NH2 in THF in an Ace
Pressure tube at 65ꢀC for 7 days.After evaporation, 10. 7 g of white crystals
were obtained (89%), mp 44–46ꢀC.IR (mineral oil) 3600–3000, 1638
1
(C¼O) cmꢂ1. H NMR (d6 DMSO) d 6.0 (s, 1H), 3.58 (m, 1H), 3.23 (s,
1H), 2.77 (d, J ¼ 4.7 Hz, 3H), 2.3 (m, 2H), 1.8 (m, 1H), 1.62 (m, 1H), 1.3
(m, 8H), 0.86 (t, J ¼ 6.9 Hz, 3H). 13C NMR (d6 DMSO) d 173.5 (C¼O), 70,
37.8, 33.8, 32.7, 32.3, 26.2, 25.7, 23, 14.8. Anal Calcd for C10H21NO2: C,
64.13: H, 11.30. Found C, 64.37; H, 11.35.
N-Ethyl-4-hydroxynonanamide (2h). g-Nonanoic lactone (1.41 g,
9 mmol) was added to a reaction tube and 15 mL of EtNH2 was added
ꢀ
to it.After 24 h at 50 C, the solution was cooled and evaporated leaving
yellowish crystals which were recrystallized from toluene/hexane leaving
1.757 g (98%) of 2h, mp 54–56ꢀC (lit.20 56–56.5ꢀC).The reaction was
repeated with a 98% yield again.IR (mineral oil) 3450–3090, 1633
1
(C¼O) cmꢂ1. H NMR (d6 DMSO) d 7.84 (s, 1H), 4.36 (d, J ¼ 5.9 Hz, 1H),
3.3 (s, 1H), 3.0 (pentet, J ¼ 6.6 Hz, 2H), 2.07 (m, 2H), 1.56 (m, 1H), 1.41 (m,
1H), 1.25 (m, 8H), 0.96 (t, J ¼ 7.3 Hz, 3H), 0.84 (t, J ¼ 7.3 Hz, 3H). 13C NMR
(d6 DMSO) d 174.2 (C¼O), 71.2, 37.9, 34.6, 33.4, 33.3, 32.2, 25.8, 22.9, 15.0,
14.3. Anal Calcd for C11H23NO2: C, 65.63: H, 11.52. Found C, 66.02;
H, 11.45.
5-Hydroxydecanamide (2i). A 1.67 g sample of d-decanolactone
(9.8 mmol) was sealed in a pressure tube with 30 mL of NH3 and the
solution was warmed to 50ꢀC for 6 days.A total of 12.74 g (70%) of
white crystals were obtained, mp 75–77ꢀC.IR (mineral oil) 3400–3200,
1695, 1607, 1464, 1130, 910, 727 and 707 cmꢂ1 1H NMR (d6 DMSO)
.
d 7.2 (s, 1H), 6.68 (s, 1H), 4.27 (d, J ¼ 5.5 Hz, CHOH), 3.3 (m, 1H),
2.0 (t, J ¼ 7.5 Hz, 2H), 1.6–1.2 (m, 12H), 0.86 (t, J ¼ 7 Hz, 3H). 13C NMR

ORDER
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2396
TAYLOR ET AL.
(d6 DMSO) d 173.9 (C¼O), 69.1, 37.0, 36.6, 35.1, 31.4, 24.8, 22.1, 21.5, 13.9.
Anal Calcd for C10H21NO2: C, 64.13; H, 11.30. Found C, 64.20, H, 11.50.
5-Hydroxyundecanamide (2j). d-Undecanolactone (0.98 g, 5.3 mmol)
was combined with 5 mL of NH3 at dry ice/acetone temperature in an Ace
Pressure tube.After 6 days at 54 ꢀC, the NH3 was evaporated at ice/acetone
temperature, and recrystallization from EtOAc gave 0.92 g of white crystals:
44 mg more crystals were obtained from the filtrate (0.966 g, 90% yield), mp
ꢂ1
81–838C.IR (mineral oil) 3400–3200, 1661, 1615, 1460 cm
1H NMR (d6
DMSO) d 7.2 (s, 1H), 6.7 (s, 1H), 4.3 (d, J ¼ 5.5 Hz, OH), 3.3 (m, 1H), 2.0 (t,
J ¼ 7 Hz, 2H), 1.6–1.2 (M, 14H), 0.85 (t, J ¼ 7 Hz, 3H). 13C NMR (d6
DMSO) d 173.9 (C ¼ O), 69.1, 37.0, 36.6, 35.1, 31.2, 28.8, 25.1, 22.0, 21.4,
13.9. Anal Calcd for C11H23NO2: C, 65.63; H, 11.52. Found, C, 65.47, H,
11.74.
5-Hydroxydodecananide (2k). d-Dodecanoiclactone (0.18 g, 9 mmol)
was combined with 10 mL of NH3 in a pressure tube and the solution was
kept at 508C for 7 days.The white crystals obtained from EtOAc weighed
0.174 g (89%), mp 88–908C.IR (mineral oil) 3400–3200, 1661, 1632, 1460,
1163, 922 cmꢂ1 1H NMR (d6 DMSO) d 7.2 (s, 1H), 6.7 (s, 1H), 4.3 (d,
J ¼ 5 Hz, OH), 3.35 (m, 1H) 2.0 (t, J ¼ 7 Hz, 2H), 1.6–1.2 (m, 16H), 0.86
(t, J ¼ 7 Hz, 3H). 13C NMR (d6 DMSO) d 173.9 (C ¼ O), 69.1, 37.0, 36.6,
35.1, 31.2, 29.1, 28.7, 25.1, 22.0, 21.4, 13.9. Anal Calcd for C12H25NO2: C,
66.93; H, 11.70. Found, C, 66.72, H, 11.99.
ACKNOWLEDGMENTS
This work was supported in part by a Glaxo-Wellcome Summer
Fellowship for N.D.I., an NSF REU grant (CHE-8804803), and a
Howard Hughes Medical Institute Faculty Development Grant.Charles
P.Kulier performed some valuable literature searches.
REFERENCES
1. Taylor, S.K.; Chmiel, N.H.Simons, L.J.; Vyvyan, J.R.
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2.The following two references are not cited by a single article in this
synthetic area,3–15 probably because they are not available in university
libraries.However, they do present some techniques that are similar to
ours.(a) Sedavkina, VA. . Motody Poluch Khim Reakt. Prep. 1974, 26,
15. CA, 86, 71871 w.(b) Sedavkina, VA. . Fiz-Khim Issled. Obl. Org.
Nek. Neorg. Soedin. 1974, 8, CA, 84, 30362 w.

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c- AND d-HYDROXYAMIDES
2397
3. Stork, G.; Zhao, K. J. Org. Chem., 1990, 112, 5875.
4.This reaction seemed to be very reliable and reproducable, but it pro-
duced only a 44% yield in our hands.We note that many high yields
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6. Sim, T.B.; Yoon, N.M. Synlett 1994, 827.
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Received in the USA November 6, 2000

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