Water → (S)-tert-Butyl 1-cyclopropyl-3-hydroxypropan-2-ylcarbamate

HRID 632208Notes

Reaction equation

HRID 632208 reaction equation
[BH4-].[Na+].[C:3]([O:7][C:8]([NH:10][C@@H:11]([CH2:16][CH:17]1[CH2:19][CH2:18]1)[C:12](OC)=[O:13])=[O:9])([CH3:6])([CH3:5])[CH3:4].O>CO>[CH:17]1([CH2:16][C@H:11]([NH:10][C:8](=[O:9])[O:7][C:3]([CH3:5])([CH3:4])[CH3:6])[CH2:12][OH:13])[CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 9834698HCID 9834698, compound

Product 1

HCID 59227079(S)-tert-Butyl 1-cyclopropyl-3-hydroxypropan-2-ylcarbamateYield 66%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

NaBH4 (1.5 g, 39 mmol) was added in portions to a solution of (S)-methyl 2-(tert-butoxycarbonylamino)-3-cyclopropylpropanoate (Example 135 a, 3.15 g, 13 mmol) in MeOH (30 mL) at room temperature. The mixture was stirred at room temperature for 2 h. H2O (50 mL) was added and a white precipitate formed. The precipitate was collected by filtration and dried to give the title product (1.84 g, 66%) as white solid which was used in the next step without further purification; MS (EI): m/e=238.1 [M+Na]+.

Workup

  1. customa white precipitate formed
  2. filtrationThe precipitate was collected by filtration
  3. customdried

Sources & evidence

ORD record
ord-9245f88dfd6d4e8394a88de584f2b857
Source dataset
uspto-grants-2016_04
Patent number
US09321727B2

Reaction notes

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