Sodium borohydride → Carbamic acid, N-(3-hydroxy-2,2-dimethylcyclobutyl)-, 1,1-dimethylethyl ester

HRID 1749410Notes

Reaction equation

HRID 1749410 reaction equation
[CH3:1][C:2]1([CH3:15])[C:5](=[O:6])[CH2:4][CH:3]1[NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11].[BH4-].[Na+]>CO>[OH:6][CH:5]1[CH2:4][CH:3]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:12])([CH3:11])[CH3:13])[C:2]1([CH3:15])[CH3:1]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 84679804Carbamic acid, N-(2,2-dimethyl-3-oxocyclobutyl)-, 1,1-dimethylethyl ester

Product 1

HCID 91636374Carbamic acid, N-(3-hydroxy-2,2-dimethylcyclobutyl)-, 1,1-dimethylethyl esterYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of tert-butyl (2,2-dimethyl-3-oxocyclobutyl)carbamate (1.0 equiv.) in MeOH (0.1 M) was added sodium borohydride (1.0 equiv.) in small portions at 0° C. After addition, the mixture was stirred at room temperature for 2 h, then the mixture was quenched with acetone. The solvent was removed under vacuum, the residue was passed through a short silica gel column chromatography (40% ethyl acetate in petroleum ether) to afford the crude title product (85% yield), which was used for the next step without further purification. MS (ESI) m/z 216.2 [M+H]+.

Workup

  1. additionAfter addition
  2. customthe mixture was quenched with acetone
  3. customThe solvent was removed under vacuum

Sources & evidence

ORD record
ord-4365bdad32434e17b7b423a0cbbfd577
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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