Sodium borohydride → (2-Hydroxymethyl-6-oxo-5,6-dihydro-1H-[1,2]diazepino[4,5,6-cd]indol-8-yl)carbamic Acid tert-butyl Ester

HRID 1064203Notes

Reaction equation

HRID 1064203 reaction equation
[C:1]([O:5][C:6](=[O:24])[NH:7][C:8]1[CH:9]=[C:10]2[C:22](=[O:23])[NH:21][N:20]=[CH:19][C:12]3=[C:13]([CH:17]=[O:18])[NH:14][C:15]([CH:16]=1)=[C:11]23)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[C:1]([O:5][C:6](=[O:24])[NH:7][C:8]1[CH:9]=[C:10]2[C:22](=[O:23])[NH:21][N:20]=[CH:19][C:12]3=[C:13]([CH2:17][OH:18])[NH:14][C:15]([CH:16]=1)=[C:11]23)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 178452623HCID 178452623, compound

Product 1

HCID 136141750(2-Hydroxymethyl-6-oxo-5,6-dihydro-1H-[1,2]diazepino[4,5,6-cd]indol-8-yl)carbamic Acid tert-butyl EsterYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of intermediate 230(a) of Example 230 (26 mg, 0.079 mmol) in methanol (2 mL) was treated with NaBH4 (6 mg, 0.16 mmol) at 0° C. for 15 min. The solution was quenched with saturated aqueous NH4Cl and diluted with ethyl acetate. After extraction, the organic phase was washed with brine, dried (Na2SO4), filtered, and concentrated. Silica gel chromatography of the residue (3:1 ethyl acetate:hexane) gave intermediate 241(a) (13 mg) in 50% yield.

Workup

  1. customThe solution was quenched with saturated aqueous NH4Cl
  2. additiondiluted with ethyl acetate
  3. extractionAfter extraction
  4. washthe organic phase was washed with brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f415be7797e74dcaaef5b13573cf0eaa
Source dataset
uspto-grants-2005_11
Patent number
US06967198B2

Reaction notes

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