Sodium borohydride → HCID 58200045, compound

HRID 1907266Notes

Reaction equation

HRID 1907266 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]([CH2:18][CH2:19][C:20]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)=[O:21])[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:9])=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([N:10]([CH2:18][CH2:19][CH:20]([C:22]2[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=2)[OH:21])[C:11](=[O:17])[O:12][C:13]([CH3:14])([CH3:16])[CH3:15])[CH3:9])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58200034HCID 58200034, compound

Product 1

HCID 58200045HCID 58200045, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of (S)-tert-butyl 1-(4-bromophenyl)ethyl(3-(4-fluorophenyl)-3-oxopropyl)carbamate (500 mg, 1.11 mmol) in MeOH (20 mL) was added an NaBH4 caplet (1 g, 26 mmol). The mixture was stirred at rt overnight and concentrated under reduced pressure. The residue was partitioned between EtOAc (80 mL) and water (20 mL). The organic layer was washed with brine, dried over Na2SO4 and concentrated to leave tert-butyl (S)-1-(4-bromophenyl)ethyl(3-(4-fluorophenyl)-3-hydroxypropyl)carbamate (474 mg, 94%) as an oil. LC-MS (3 min) tR=2.33 min, 454. 452, 380, 378.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was partitioned between EtOAc (80 mL) and water (20 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d59c18dcd2754bef9c50a6a6f23bdead
Source dataset
uspto-grants-2013_12
Patent number
US08598160B2

Reaction notes

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