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

HRID 860094Notes

Reaction equation

HRID 860094 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-4b1d0b92cb0c4fde8e5b31e49d004e82
Source dataset
uspto-grants-2006_12
Patent number
US07153862B2

Reaction notes

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