Sodium borohydride → HCID 66982361, compound

HRID 516263Notes

Reaction equation

HRID 516263 reaction equation
[CH:1]1([C:4]2[C:14]3[CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10][CH2:9][C:8]=3[CH:7]=[C:6]3[O:22][CH2:23][CH2:24][N:25]([CH2:26][CH2:27][O:28][C:29]4[C:34]([F:35])=[CH:33][C:32]([CH:36]=[O:37])=[CH:31][C:30]=4[F:38])[C:5]=23)[CH2:3][CH2:2]1.[BH4-].[Na+]>CO>[CH:1]1([C:4]2[C:14]3[CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])[CH2:10][CH2:9][C:8]=3[CH:7]=[C:6]3[O:22][CH2:23][CH2:24][N:25]([CH2:26][CH2:27][O:28][C:29]4[C:30]([F:38])=[CH:31][C:32]([CH2:36][OH:37])=[CH:33][C:34]=4[F:35])[C:5]=23)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86658950HCID 86658950, compound

Product 1

HCID 66982361HCID 66982361, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 270 mg of t-butyl 5-cyclopropyl-4-[2-(2,6-difluoro-4-formylphenoxy)ethyl]-3,4,6,7,9,10-hexahydro[1,4]oxazino[2,3-h][3]benzazepine-8(2H)-carboxylate in 6 ml of MeOH was added 30 mg of sodium borohydride, followed by stirring at room temperature for 4 hours. The reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel chromatography (elution solvent: HEX-EtOAc)) to obtain 220 mg of t-butyl 5-cyclopropyl-4-{2-[2,6-difluoro-4-(hydroxymethyl)phenoxy]ethyl}-3,4,6,7,9,10-hexahydro[1,4]oxazino[2,3-h][3]benzazepine-8(2H)-carboxylate as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel chromatography (elution solvent: HEX-EtOAc))

Sources & evidence

ORD record
ord-bb6a76111b01492292036c299dbf21ab
Source dataset
uspto-grants-2015_08
Patent number
US09108977B2

Reaction notes

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