Sodium borohydride → HCID 69417629, compound

HRID 1375093Notes

Reaction equation

HRID 1375093 reaction equation
[C:1]([O:5][C:6](=[O:30])[CH2:7][C:8]1([C:13]2[CH:18]=[CH:17][C:16]([NH:19][CH2:20]N3C4C=CC=CC=4N=N3)=[CH:15][CH:14]=2)[CH2:12][CH2:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>C(O)C>[C:1]([O:5][C:6](=[O:30])[CH2:7][C:8]1([C:13]2[CH:18]=[CH:17][C:16]([NH:19][CH3:20])=[CH:15][CH:14]=2)[CH2:12][CH2:11][CH2:10][CH2:9]1)([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydride3×HCID 86590648HCID 86590648, compound

Product 1

HCID 69417629HCID 69417629, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred suspension of [1-(4-{(benzotriazol-1-ylmethyl)-amino}-phenyl)-cyclopentyl]-acetic acid tert-butyl ester (0.21 g) in ethanol (10 mL), under argon, was treated with sodium borohydride (0.051 g). After stirring at room temperature for 2 hours a further aliquot of sodium borohydride (0.017 g) was added and stirring was continued for a further hour, then a further aliquot of sodium borohydride (0.017 g) was added and stirring was continued for a further hour. The reaction mixture was then evaporated and the residue was treated with water (15 mL) and ethyl acetate (25 mL). The organic phase was separated and then washed with water (15 mL), then with brine (15 mL), then dried over magnesium sulfate and then evaporated to give the title compound (0.15 g) as an amber oil which crystallised on standing.

Workup

  1. additionwas added
  2. waitwas continued for a further hour
  3. stirringstirring
  4. waitwas continued for a further hour
  5. customThe reaction mixture was then evaporated
  6. additionthe residue was treated with water (15 mL) and ethyl acetate (25 mL)
  7. customThe organic phase was separated
  8. washwashed with water (15 mL)
  9. dry with materialwith brine (15 mL), then dried over magnesium sulfate
  10. customevaporated

Sources & evidence

ORD record
ord-4f0d6d84fe434e1cad382bd17dcbb38a
Source dataset
uspto-grants-2007_01
Patent number
US07166616B2

Reaction notes

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