Sodium borohydride → 1,1-Dimethylethyl cyclopropyl{[2,3-dichloro-5-(hydroxymethyl)phenyl]methyl}carbamate

HRID 337567Notes

Reaction equation

HRID 337567 reaction equation
[CH:1]1([N:4]([CH2:12][C:13]2[CH:18]=[C:17]([CH:19]=[O:20])[CH:16]=[C:15]([Cl:21])[C:14]=2[Cl:22])[C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8])[CH2:3][CH2:2]1.[BH4-].[Na+]>CO>[CH:1]1([N:4]([CH2:12][C:13]2[CH:18]=[C:17]([CH2:19][OH:20])[CH:16]=[C:15]([Cl:21])[C:14]=2[Cl:22])[C:5](=[O:11])[O:6][C:7]([CH3:9])([CH3:10])[CH3:8])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 866516631,1-Dimethylethyl cyclopropyl[(2,3-dichloro-5-formylphenyl)methyl]carbamate

Product 1

HCID 668961381,1-Dimethylethyl cyclopropyl{[2,3-dichloro-5-(hydroxymethyl)phenyl]methyl}carbamate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a methanol (0.16 M) solution of 1,1-dimethylethyl cyclopropyl[(2,3-dichloro-5-formylphenyl)methyl]carbamate from the previous step was added at 0° C. sodium borohydride (1.3 eq.). The resulting solution was stirred at 0° C. for 2 h before the volatiles were removed in vacuo. The resulting residue was then partitioned between ether and 1 N aq. HCl. The aqueous layer was separated and back-extracted with ether. The combined organic extracts were washed further with water and brine, dried over Na2SO4, filtered and the filtrate concentrated in vacuo. Purification of the crude product thus obtained by way of flash chromatography (SiO2, Hex→3:7 (v/v) Hex:EtOAc) afforded the title compound as a colorless oil.

Workup

  1. customwere removed in vacuo
  2. customThe resulting residue was then partitioned between ether and 1 N aq. HCl
  3. customThe aqueous layer was separated
  4. extractionback-extracted with ether
  5. washThe combined organic extracts were washed further with water and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated in vacuo
  9. customPurification of the crude product
  10. customthus obtained by way of flash chromatography (SiO2, Hex→3:7 (v/v) Hex:EtOAc)

Sources & evidence

ORD record
ord-92793f81f60c4a7caf039c3f2bfcc079
Source dataset
uspto-grants-2014_11
Patent number
US08889714B2

Reaction notes

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