Sodium borohydride → tert-Butyl (1S,2S)-3-bromo-1-(3,5-difluorobenzyl)-2-hydroxypropylcarbamate

HRID 14004Notes

Reaction equation

HRID 14004 reaction equation
[BH4-].[Na+].[Br:3][CH2:4][C:5](=[O:24])[C@@H:6]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:7][C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[C:10]([F:15])[CH:9]=1>C(OCC)(=O)C.CCCCCC>[Br:3][CH2:4][C@@H:5]([OH:24])[C@@H:6]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:20])([CH3:21])[CH3:22])[CH2:7][C:8]1[CH:9]=[C:10]([F:15])[CH:11]=[C:12]([F:14])[CH:13]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 57484758HCID 57484758, compound

Product 1

HCID 57487171tert-Butyl (1S,2S)-3-bromo-1-(3,5-difluorobenzyl)-2-hydroxypropylcarbamate

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Sodium borohydride (1.32 g, 34.9 mmole, 1.1 eq.) is added to tert-Butyl (1S)-3-bromo-1-(3,5-difluorobenzyl)-2-oxopropylcarbamate (III, EXAMPLE 1, 12 g, 31.75 mmole) dissolved in absolute alcohol (500 mL) at −78 degrees C. The reaction mixture is stirred for 0.5 hour and monitored by TLC (ethyl acetate/hexane, 20/80; Rf=0.2). The mixture is quenched with water (10 mL) and the solvent removed under reduced pressure with heat (not exceeding 30 degrees C.) to dryness. The solid is partitioned between dichloromethane and water, washed with saline, dried over anhydrous sodium sulfate. The solvent is removed under reduced pressure to give the title compound, TLC (ethyl acetate/hexane, 20/80) Rf=0.2; MS (MH+)=381.2.

Workup

  1. customThe mixture is quenched with water (10 mL)
  2. customthe solvent removed under reduced pressure
  3. temperaturewith heat (not
  4. customexceeding 30 degrees C
  5. customThe solid is partitioned between dichloromethane and water
  6. washwashed with saline
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-56c8d84b05a244a49c9d981489666bb4
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Reaction notes

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