Sodium borohydride → HCID 131734576, compound

HRID 595248Notes

Reaction equation

HRID 595248 reaction equation
[BH4-].[Na+].[Cl:3][CH2:4][C:5](=[O:16])[C@H:6]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH3:7]>CO.C(O)(=O)C>[Cl:3][CH2:4][CH:5]([OH:16])[C@H:6]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:13])([CH3:12])[CH3:14])[CH3:7]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 964820041522241-50-4

Product 1

HCID 131734576HCID 131734576, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Sodium borohydride (621 mg, 16.42 mmol) was added to a mixture of (R)-tert-butyl (4-chloro-3-oxobutan-2-yl)carbamate (910 mg, 4.10 mmol) in methanol (9 mL) at 0° C., and the mixture was stirred for one hour at 0° C. A few drops of acetic acid were added then the mixture was concentrated under reduced pressure. The residue was diluted with ethyl acetate, washed with water, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to afford tert-butyl ((2R)-4-chloro-3-hydroxybutan-2-yl)carbamate. 1H NMR (500 MHz, DMSO-d6) δ 6.65 (d, J=8.1 Hz, 1H), 5.24 (d, J=5.6 Hz, 1H), 3.58-3.53 (m, 1H), 3.50-3.44 (m, 2H), 3.44-3.34 (m, 1H), 1.36 (s, 9H), 0.99 (d, J=6.3, 3H).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. additionThe residue was diluted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2c85c12eda7848878505f9c88efef5ce
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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