Borane;tetrahydrofuran → Benzyl 1-hydroxy-3-(1-methylcyclohexyl)propan-2-ylcarbamate

HRID 451787Notizen

Reaktionsgleichung

[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH2:16][C:17]1([CH3:23])[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)[C:13](O)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B.C1COCC1>C1COCC1>[OH:14][CH2:13][CH:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:16][C:17]1([CH3:23])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

A mixture of 0.510 g (1.60 mmol) of 2-(benzyloxycarbonylamino)-3-(1-methylcyclohexyl)propanoic acid, 5 mL of THF, and 10 mL of 1.0 M BH3.THF in THF was stirred at 0° C. for 2 h. The mixture was allowed to warm to rt for 16 h. The reaction mixture was then cooled with an ice bath and quenched with 20 mL of MeOH and 2 mL of HOAc. After the solvents were removed in vacuo, the residue was purified by reversed-phase HPLC to afford 0.3655 g (75%) of benzyl 1-hydroxy-3-(1-methylcyclohexyl)propan-2-ylcarbamate. MS ESI +ve m/z 328 (M+Na).

Aufarbeitung

temperatureto warm to rt for 16 h
temperatureThe reaction mixture was then cooled with an ice bath
customquenched with 20 mL of MeOH and 2 mL of HOAc
customAfter the solvents were removed in vacuo
customthe residue was purified by reversed-phase HPLC

Quellen und Nachweise

ORD-Eintrag: ord-8b2142009ffa44f78159151b32d9cd8d
Quelldatensatz: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08487108B2

Notizen zur Reaktion

Wird geladen…