Sodium borohydride → HCID 58109353, compound

HRID 2037593Notes

Reaction equation

HRID 2037593 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C@@H:8]([N:10]2[CH2:15][CH2:14][C@@:13]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)([CH2:16][C:17](=[O:19])[CH3:18])[O:12][C:11]2=[O:27])[CH3:9])[CH:5]=[CH:6][CH:7]=1.[BH4-].[Na+]>C1COCC1.CO>[Br:1][C:2]1[CH:3]=[C:4]([C@@H:8]([N:10]2[CH2:15][CH2:14][C@@:13]([C:20]3[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=3)([CH2:16][CH:17]([OH:19])[CH3:18])[O:12][C:11]2=[O:27])[CH3:9])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58109464HCID 58109464, compound

Product 1

HCID 58109353HCID 58109353, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of (S)-3-((S)-1-(3-bromophenyl)ethyl)-6-(4-fluorophenyl)-6-(2-oxopropyl)-1,3-oxazinan-2-one (12 mg, 0.028 mmol) in 3:1 THF/MeOH (4 mL) was cooled to 0° C. NaBH4 (2.1 mg, 2 equiv) was added. After 15 min, the mixture was warmed to rt slowly. After stirring 1.5 h, LC-MS found the reaction completed. The mixture was quenched by water (2 mL), concentrated, and purified by preparative HPLC to afford (6S)-3-((S)-1-(3-bromophenyl)ethyl)-6-(4-fluorophenyl)-6-(2-hydroxypropyl)-1,3-oxazinan-2-one (4.4 mg, 36%). LC-MS (3 min) tR=1.68 min, m/z=458, 460 (M+Na). 1H NMR (CDCl3) 7.36-7.21 (m, 3H), 7.12-6.96 (m, 4H), 6.83 (m, 1H), 5.63 (m, 1H), 2.93 (m, 1H), 1.51 (d, 3H), 1.17 (d, 3H).

Workup

  1. customThe mixture was quenched by water (2 mL)
  2. concentrationconcentrated
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-7500be7c9ffd450dbffcdb3cab270faa
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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