(Dimethyl sulfide)trihydroboron → rel-1,1-Dimethylethyl N-[(1R,3R)-3-(hydroxymethyl)cyclohexyl]carbamate
Reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][CH2:12][C@H:11]([C:15](O)=[O:16])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CSC.B>C1COCC1>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]1[CH2:14][CH2:13][CH2:12][C@H:11]([CH2:15][OH:16])[CH2:10]1)([CH3:4])([CH3:2])[CH3:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
Racemic trans 3-tert-butoxycarbonylamino-cyclohexanecarboxylic acid (1 g, 4.11 mmol) was dissolved in THF (30 mL) and borane dimethylsulfide 2M in THF (3 mL, 6 mmol) was added slowly. The resulting colorless solution was stirred at 40° C. After 4 hours the reaction mixture was cooled to 0° C., quenched by addition of saturated aqueous NaHCO3, and extracted twice with EtOAc. The combined organic layers were dried (Na2SO4), filtered and evaporated to give 0.905 g of crude racemic trans 3-hydroxymethyl-cyclohexyl-carbamic acid tert-butyl ester as a colorless oil (>95% yield).
Workup
- temperatureAfter 4 hours the reaction mixture was cooled to 0° C.
- customquenched by addition of saturated aqueous NaHCO3
- extractionextracted twice with EtOAc
- dry with materialThe combined organic layers were dried (Na2SO4)
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-a0a8bbd672774fa5885553164aa5ea93
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08012974B2
Reaction notes
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