Sodium borohydride → HCID 86611579, compound

HRID 1432081Notes

Reaction equation

HRID 1432081 reaction equation
[Cl:1][CH2:2][C:3]([C@H:5]([NH:13][C:14]([C@@H:16]([N:18]([CH3:27])[C:19](=[O:26])[CH2:20][CH2:21][CH2:22][CH2:23][CH:24]=[CH2:25])[CH3:17])=[O:15])[CH2:6][CH:7]([CH3:12])[CH2:8][CH2:9][CH:10]=[CH2:11])=[O:4].[BH4-].[Na+]>C(O)C>[Cl:1][CH2:2][CH:3]([C@H:5]([NH:13][C:14]([C@@H:16]([N:18]([CH3:27])[C:19](=[O:26])[CH2:20][CH2:21][CH2:22][CH2:23][CH:24]=[CH2:25])[CH3:17])=[O:15])[CH2:6][CH:7]([CH3:12])[CH2:8][CH2:9][CH:10]=[CH2:11])[OH:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86611580HCID 86611580, compound

Product 1

HCID 86611579HCID 86611579, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 3.15 g (5 mmol) hept-6-enoic acid {(S)-1-[(R)-1-(2-chloro-acetyl)-3-methyl-hept-6-enylcarbamoyl]-ethyl}methyl-amide in 110 ml ethanol is added to a suspension of 378 mg (10 mmol) sodium borohydride in 30 ml ethanol at −78° C. The temperature is kept below −75° C. during the addition and the mixture is stirred for an additional hour. The reaction is quenched with 25 ml 1 M HCl at −78° C. and the mixture is allowed to warm to rt. After evaporation of the ethanol and addition of 50 ml 1 M HCl the mixture is extracted with EtOAc. The organic layer is washed with 1 M HCl and a half-saturated aqueous sodium chloride solution, dried with sodium sulfate and evaporated. Purification by chromatography on silica gel (cyclohexane/EtOAc 70/30 to 50/50) gives the desired product as a brown oil (mixture of diastereomers).

Workup

  1. additionThe temperature is kept below −75° C. during the addition
  2. customThe reaction is quenched with 25 ml 1 M HCl at −78° C.
  3. customAfter evaporation of the ethanol and addition of 50 ml 1 M HCl the mixture
  4. extractionis extracted with EtOAc
  5. washThe organic layer is washed with 1 M HCl
  6. dry with materiala half-saturated aqueous sodium chloride solution, dried with sodium sulfate
  7. customevaporated
  8. customPurification by chromatography on silica gel (cyclohexane/EtOAc 70/30 to 50/50)

Sources & evidence

ORD record
ord-8b7ef2cb98ca481d8da1f123910fdbd1
Source dataset
uspto-grants-2009_11
Patent number
US07612055B2

Reaction notes

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