Ammonium Chloride → tert-butyl 1-((2S)-2-{[(benzyloxy)carbonyl]amino}-1-hydroxybutyl)cyclopropanecarboxylate

HRID 1173611Notes

Reaction equation

[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:25][CH3:26])[C:13]([C:15]1([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:17][CH2:16]1)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].[Cl-].[NH4+]>CO>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:25][CH3:26])[CH:13]([C:15]1([C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])[CH2:17][CH2:16]1)[OH:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of tert-butyl 1-((2S)-2-{[(benzyloxy)carbonyl]amino}butanoyl)cyclopropanecarboxylate (1.16 g) in methanol (25 mL) was added sodium borohydride (180 mg) at 0° C., and the mixture was stirred at 0° C. for 30 min. Aqueous ammonium chloride was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=50/1→1/1) to give tert-butyl 1-((2S)-2-{[(benzyloxy)carbonyl]amino}-1-hydroxybutyl)cyclopropanecarboxylate as a colorless oil (yield: 914.8 mg, yield: 78%).

Workup

extractionthe mixture was extracted with ethyl acetate
dry with materialThe extract was dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=50/1→1/1)

Sources & evidence

ORD record: ord-525d4496337843718dd19910e8a1de32
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07834051B2

Reaction notes

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