Ammonia → Cyclohexanecarboxamide, 3-amino-4-hydroxy-N,N-dimethyl-, (1S,3R,4R)-

HRID 707488Notes

Reaction equation

HRID 707488 reaction equation
[NH3:1].[CH3:2][N:3]([CH3:13])[C:4]([C@H:6]1[CH2:12][CH2:11][C@@H:10]2[C@@H:8]([O:9]2)[CH2:7]1)=[O:5]>>[NH2:1][C@H:8]1[C@H:10]([OH:9])[CH2:11][CH2:12][C@H:6]([C:4]([N:3]([CH3:13])[CH3:2])=[O:5])[CH2:7]1

Participants

3

Reactant 2

HCID 222AmmoniaHCID 58084195(1S,3S,6R)-N,N-dimethyl-7-oxabicyclo[4.1.0]heptane-3-carboxamide

Product 1

HCID 66657052Cyclohexanecarboxamide, 3-amino-4-hydroxy-N,N-dimethyl-, (1S,3R,4R)-

Conditions

Temperature
40 °C

Procedure

A 28% aqueous ammonia solution (5 ml) was added to (1S,3S,6R)—N,N-dimethyl-7-oxabicyclo[4.1.0]heptane-3-carboxamide (5) (1 g) at room temperature. The mixed solution was stirred at 40° C. for hours, and then, the solvent was concentrated under reduced pressure to obtain (1S,3R,4R)-3-amino-4-hydroxy-N,N-dimethylcyclohexanecarboxamide (1.18 g).

Workup

  1. concentrationthe solvent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1c5cf4d8c90c4f1eba1ec597ed93f9b4
Source dataset
uspto-grants-2015_11
Patent number
US09175012B2

Reaction notes

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