Sodium borohydride → [6-Hydroxy-8-(2-methyl-pyrimidin-5-yl)-oct-7-enyl]-carbamic acid tert-butyl ester

HRID 2120702Notes

Reaction equation

HRID 2120702 reaction equation
[C:1]([O:5][C:6](=[O:24])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13](=[O:23])[CH:14]=[CH:15][C:16]1[CH:17]=[N:18][C:19]([CH3:22])=[N:20][CH:21]=1)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>C1COCC1.CO>[C:1]([O:5][C:6](=[O:24])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([OH:23])[CH:14]=[CH:15][C:16]1[CH:17]=[N:18][C:19]([CH3:22])=[N:20][CH:21]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 73687172[8-(2-Methyl-pyrimidin-5-yl)-6-oxo-oct-7-enyl]-carbamic acid tert-butyl ester

Product 1

HCID 73687171[6-Hydroxy-8-(2-methyl-pyrimidin-5-yl)-oct-7-enyl]-carbamic acid tert-butyl esterYield 70.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 24-3 (1.419 g, 4.255 mmol) in THF (10 mL) and methanol (5 mL) was treated with sodium borohydride (162.0 mg, 4.282 mmol) and stirred at room temperature (1 h). The reaction was quenched with acetone and the solvent removed in vacuo. Purification via silica chromatography (hexane/ethyl acetate) afforded the title compound 24-4 (1.0 g).

Workup

  1. customThe reaction was quenched with acetone
  2. customthe solvent removed in vacuo
  3. customPurification via silica chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-cb6a1a2b8ec4457ab8b3997e513c5737
Source dataset
uspto-grants-2004_02
Patent number
US06693101B2

Reaction notes

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