Ammonia → (1S,3S,4R)-4-Bromo-3-hydroxycyclohexanecarboxylic amide

HRID 723537Notes

Reaction equation

HRID 723537 reaction equation
[Br:1][C@H:2]1[C@@H:8]2[CH2:9][C@@H:5]([C:6](=[O:10])[O:7]2)[CH2:4][CH2:3]1.[NH3:11].CO>C1COCC1>[Br:1][C@@H:2]1[CH2:3][CH2:4][C@H:5]([C:6]([NH2:11])=[O:10])[CH2:9][C@@H:8]1[OH:7]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 10878278(1S,4R,5S)-4-Bromo-6-oxabicyclo[3.2.1]octan-7-one

Product 1

HCID 69375303(1S,3S,4R)-4-Bromo-3-hydroxycyclohexanecarboxylic amide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(1S,4R,5S)-4-Bromo-6-oxabicyclo[3.2.1]octan-7-one (352a) (2.88 g, 14.0 mmol) was taken up in THF (27 mL) and treated with 0.880 ammonia (7.1 mL) at 20° C. for 24 h with stirring. The solvent was then removed in vacuo to give a white solid in quantitative yield; [α]D=−55.4° (c=1, MeOH).

Workup

  1. customThe solvent was then removed in vacuo
  2. customto give a white solid in quantitative yield

Sources & evidence

ORD record
ord-29699c1d13014cd09ede5b0449092600
Source dataset
uspto-grants-2006_11
Patent number
US07141564B2

Reaction notes

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