Sodium borohydride → Tert-butyl (1-{5-chloro-3-[6-(hydroxymethyl)pyridin-3-yl]-2-methoxy-4-methylphenyl}ethyl)carbamate

HRID 510988Notes

Reaction equation

HRID 510988 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[C:5]([CH3:30])=[C:6]([C:22]2[CH:23]=[N:24][C:25]([CH:28]=[O:29])=[CH:26][CH:27]=2)[C:7]([O:20][CH3:21])=[C:8]([CH:10]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH3:11])[CH:9]=1>CO>[Cl:3][C:4]1[C:5]([CH3:30])=[C:6]([C:22]2[CH:23]=[N:24][C:25]([CH2:28][OH:29])=[CH:26][CH:27]=2)[C:7]([O:20][CH3:21])=[C:8]([CH:10]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:16])[CH3:17])[CH3:11])[CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86666904Tert-butyl {1-[5-chloro-3-(6-formylpyridin-3-yl)-2-methoxy-4-methylphenyl]ethyl}carbamate

Product 1

HCID 86666905Tert-butyl (1-{5-chloro-3-[6-(hydroxymethyl)pyridin-3-yl]-2-methoxy-4-methylphenyl}ethyl)carbamate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Sodium tetrahydroborate (2.8 mg, 0.074 mmol) was added to a mixture of tert-butyl {1-[5-chloro-3-(6-formylpyridin-3-yl)-2-methoxy-4-methylphenyl]ethyl}carbamate (20 mg, 0.05 mmol) in methanol (2 mL) at 0° C. The reaction was stirred for 1 h at 0° C. The reaction mixture was partitioned between water and EtOAc. The combined organic layers was washed with brine, dried over MgSO4, filtered and concentrated to give crude product. This crude was used for next step.

Workup

  1. customThe reaction mixture was partitioned between water and EtOAc
  2. washThe combined organic layers was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give crude product

Sources & evidence

ORD record
ord-6846d4c4e1d44bb7985d42b902374084
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

Loading…