Ammonia → (1S,3S,4R)-4-Bromo-3-hydroxycyclohexanecarboxylic amide
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
Product 1
Reagents, catalysts & solvents 1
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
- customThe solvent was then removed in vacuo
- 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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