Sodium borohydride → tert-Butyl 3-(4-bromophenyl)-1-hydroxypropan-2-ylcarbamate

HRID 1429361Notes

Reaction equation

HRID 1429361 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:10](OC)=[O:11])=[CH:4][CH:3]=1.[Li]Cl.O.[BH4-].[Na+]>C(O)C.C1COCC1>[C:18]([O:17][C:15](=[O:16])[NH:14][CH:9]([CH2:10][OH:11])[CH2:8][C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1)([CH3:19])([CH3:21])[CH3:20]

Participants

6

Reactant 3

HCID 4311764Sodium borohydrideHCID 15735975Methyl 3-(4-bromophenyl)-2-((tert-butoxycarbonyl)amino)propanoateHCID 178526217HCID 178526217, compound

Product 1

HCID 57594209tert-Butyl 3-(4-bromophenyl)-1-hydroxypropan-2-ylcarbamateYield 94%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 3e (15 g, 42 mmol) in ethanol (50 mL) and THF (50 mL) was added LiCl.H2O (10 g, 170 mmol) and NaBH4 (6.3 g, 170 mmol) at 0° C. The mixture was stirred at rt overnight. LCMS analysis indicated the total consumption of compound 3e. The precipitate was removed by filtration and the filtrate was concentrated in vacuo to give 3f as a white solid (13 g, 94% yield).

Workup

  1. customthe total consumption of compound 3e
  2. customThe precipitate was removed by filtration
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-80b44040b6cc4bdfa5599cfc727a3473
Source dataset
uspto-grants-2015_01
Patent number
US08940722B2

Reaction notes

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