Water → HCID 86761355, compound

HRID 1010919Notes

Reaction equation

HRID 1010919 reaction equation
[C:1]([O:5][C:6](=[O:35])[NH:7][C@H:8]([C:10]1[CH:15]=[CH:14][C:13]([C:16]([CH:18]2[CH2:21][N:20]([CH:22]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:19]2)=[O:17])=[CH:12][CH:11]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].O>O1CCCC1.CO>[C:23]1([CH:22]([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[N:20]2[CH2:21][CH:18]([CH:16]([OH:17])[C:13]3[CH:14]=[CH:15][C:10]([C@@H:8]([NH:7][C:6](=[O:35])[O:5][C:1]([CH3:2])([CH3:4])[CH3:3])[CH3:9])=[CH:11][CH:12]=3)[CH2:19]2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 131729015HCID 131729015, compound

Product 1

HCID 86761355HCID 86761355, compoundYield 6.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

9.94 g of the compound [88-1] was dissolved in 100 mL of tetrahydrofuran and 20 mL of methanol, 799 mg of sodium borohydride was added thereto at room temperature, and the mixture was stirred at the same temperature for 2.5 hours. To the reaction mixture, water was added, and the mixture was extracted with chloroform. The obtained organic layer was dried over anhydrous magnesium sulfate. Then, the insolubles were filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=100/0 to 30/70) to obtain 632 mg of tert-butyl ((1S)-1-{4-[[1-(diphenyl methyl)azetidin-3-yl](hydroxy)methyl]phenyl}ethyl)carbamate [88-2] (hereinafter, referred to as the compound [88-2]).

Workup

  1. extractionthe mixture was extracted with chloroform
  2. dry with materialThe obtained organic layer was dried over anhydrous magnesium sulfate
  3. filtrationThen, the insolubles were filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=100/0 to 30/70)

Sources & evidence

ORD record
ord-5f9c33a204b54c8ead8cd4fcfc2f6ad3
Source dataset
uspto-grants-2011_07
Patent number
US07977336B2

Reaction notes

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