Sodium borohydride → HCID 86586680, compound

HRID 2088148Notes

Reaction equation

HRID 2088148 reaction equation
[BH4-].[Na+].[CH2:3]([N:10]1[C@@H:15]2[C:16](=[O:18])[CH2:17][C@@:11]1([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C@H:12]([O:19][CH2:20][C:21]1[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[C:23]([C:31]([F:34])([F:33])[F:32])[CH:22]=1)[CH2:13][CH2:14]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CO>[CH2:3]([N:10]1[C@@H:15]2[C@@H:16]([OH:18])[CH2:17][C@@:11]1([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C@H:12]([O:19][CH2:20][C:21]1[CH:26]=[C:25]([C:27]([F:29])([F:30])[F:28])[CH:24]=[C:23]([C:31]([F:32])([F:33])[F:34])[CH:22]=1)[CH2:13][CH2:14]2)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86586679HCID 86586679, compound

Product 1

HCID 86586680HCID 86586680, compoundYield 72.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (55 mg, 1.44 mmol) was added to a stirred solution of (1R*,2R*,5S*)-8-benzyl-2-{[3,5-bis(trifluoromethyl)phenyl]methoxy}-1-phenyl-8-azabicyclo[3.2.1]octan-6-one (Example 41; 50 mg 0.09 mmol) in methanol (3 ml) at +5° C. The reaction mixture was stirred for 15 minutes and quenched with saturated aqueous NaHCO3 and extracted into dichloromethane. The combined organic extracts were dried (Na2SO4) and concentrated. The residue was purified by chromatography on silica gel (iso-hexane:diethyl ether 10-45%) to give the title, compound (35 mg, 70%).

Workup

  1. customquenched with saturated aqueous NaHCO3
  2. extractionextracted into dichloromethane
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography on silica gel (iso-hexane:diethyl ether 10-45%)

Sources & evidence

ORD record
ord-c610a12a847a4b80b9984de19e608215
Source dataset
uspto-grants-2004_04
Patent number
US06727249B2

Reaction notes

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