Ammonium Chloride → HCID 78035270, compound

HRID 1422605Notes

Reaction equation

[CH3:1][O:2][C:3]([NH:5][C:6]1([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=2)[CH2:8][CH:7]1[CH2:9][C:10](OCC)=[O:11])=[O:4].[BH4-].[Li+].[NH4+].[Cl-]>O1CCCC1>[OH:11][CH2:10][CH2:9][CH:7]1[CH2:8][C:6]1([NH:5][C:3](=[O:4])[O:2][CH3:1])[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=1

Participants

Conditions

Temperature: 23 °C

Procedure

Ethyl 2-((1SR,2SR)-2-(methoxycarbonylamino)-2-(3-nitrophenyl)cyclopropyl)acetate (intermediate B10a) (2.45 g, 7.6 mmol, Eq: 1.00) was dissolved in tetrahydrofuran (80 ml) and lithium borohydride (2 M in THF; 8.36 ml, 16.7 mmol, Eq: 2.2) was added dropwise at 5° C. The turbid solution was stirred at 23° C. for 6 hours. The reaction mixture was poured into ice water, sat NH4Cl solution (100 ml) was added slowly and the mixture was stirred vigorously for 45 min (gas evolution finished). Then extraction with EtOAc, the organic layer was dried over Na2SO4, filtration and evaporation of the solvent left a yellow oil (2.5 g; 117%). Crystallization with dichloromethane/cyclohexane gives the methyl (1SR,2SR)-2-(2-hydroxyethyl)-1-(3-nitrophenyl)cyclopropylcarbamate (1.84 g, 6.56 mmol, 86.4% yield) as a light yellow solid. MS (ISP): m/z=281.1 [(M+H)+].

Workup

additionwas added slowly
stirringthe mixture was stirred vigorously for 45 min (gas evolution finished)
extractionThen extraction with EtOAc
dry with materialthe organic layer was dried over Na2SO4, filtration and evaporation of the solvent
waitleft a yellow oil (2.5 g; 117%)
customCrystallization with dichloromethane/cyclohexane

Sources & evidence

ORD record: ord-ea16452afe71438a999d2d1eeecd908d
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08927535B2

Reaction notes

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