Sodium borohydride → (5)-Tert-butyl 3-(3-(hydroxymethyl)phenyl)-1-((4-methoxyphenyl)(methyl)amino)-1-oxopropan-2-ylcarbamate

HRID 1471636Notes

Reaction equation

HRID 1471636 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]([CH2:9][C@H:10]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[C:11]([N:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)[CH3:14])=[O:12])[CH:6]=[CH:7][CH:8]=1)=[O:2].[BH4-].[Na+]>CO>[OH:2][CH2:1][C:3]1[CH:4]=[C:5]([CH2:9][C@H:10]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:28])([CH3:27])[CH3:29])[C:11]([N:13]([C:15]2[CH:16]=[CH:17][C:18]([O:21][CH3:22])=[CH:19][CH:20]=2)[CH3:14])=[O:12])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 90289977(S)-tert-Butyl 3-(3-formylphenyl)-1-((4-methoxyphenyl)(methyl)amino)-1-oxopropan-2-ylcarbamate

Product 1

HCID 90289960(5)-Tert-butyl 3-(3-(hydroxymethyl)phenyl)-1-((4-methoxyphenyl)(methyl)amino)-1-oxopropan-2-ylcarbamate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

(S)-tert-Butyl 3-(3-formylphenyl)-1-((4-methoxyphenyl)(methyl)amino)-1-oxopropan-2-ylcarbamate (2.71 g, 6.58 mmole) was dissolved in methanol (66 ml). The solution was cooled to 0° C. in an ice bath. NaBH4 was added to the cooled solution and the resulting reaction mixture was stirred for 30 min. The reaction was confirmed to be complete by tlc and HPLC/MS. The reaction was concentrated under reduced pressure and then partitioned between EtOAc and H2O. The aqueous layer was extracted with EtOAc (2×). The combined organics were washed with H2O (2×) and brine (2×). The organic layer was dried over MgSO4, filtered and concentrated. The crude product was purified by flash column using EtOAc/hexanes. Yield=1.3 g. MS (m/z) 415 [M+14]+.

Workup

  1. customthe resulting reaction mixture
  2. concentrationThe reaction was concentrated under reduced pressure
  3. custompartitioned between EtOAc and H2O
  4. extractionThe aqueous layer was extracted with EtOAc (2×)
  5. washThe combined organics were washed with H2O (2×) and brine (2×)
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by flash column

Sources & evidence

ORD record
ord-34b26d4aad2442e49aee76cc96084bee
Source dataset
uspto-grants-2015_04
Patent number
US09012441B2

Reaction notes

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