(2S)-2-(((tert-butoxy)carbonyl)amino)-3-cyclohexylpropanoic acid → (S)-(-)-2-(tert-Butoxycarbonylamino)-3-cyclohexyl-1-propanol
Reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]>O1CCCC1>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]([CH2:10][OH:11])[CH2:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)([CH3:2])([CH3:4])[CH3:3]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of (2S)-2-[(tert-butoxycarbonyl)amino]-3-cyclohexylpropanoic acid (5.0 g, 18 mmol) in tetrahydrofuran (50 mL) at 0° C. was added 1.0 M borane-THF complex in THF (55.3 mL, 55.3 mmol). After addition, the reaction mixture was stirred at room temperature for 3 hours, then cooled down with an ice-bath, and quenched by the slow addition of AcOH:MeOH (1:5, 40 mL). Then the mixture was warmed to room temperature for 2 hours. The THF volume was reduced by ½ and the product was partitioned between saturated aqueous NaHCO3 and DCM. The combined organic fractions were dried over Na2SO4 and concentrated under reduced pressure to give an oil residue which was used directly in the next reaction without further purification. LC-MS found: 168.1 (M−Boc)+.
Workup
- additionAfter addition
- temperaturecooled down with an ice-bath
- customquenched by the slow addition of AcOH:MeOH (1:5, 40 mL)
- temperatureThen the mixture was warmed to room temperature for 2 hours
- customthe product was partitioned between saturated aqueous NaHCO3 and DCM
- dry with materialThe combined organic fractions were dried over Na2SO4
- concentrationconcentrated under reduced pressure
- customto give an oil residue which
- customwas used directly in the next reaction without further purification
Sources & evidence
- ORD record
- ord-604b93dfb73448a199d9c106a736147e
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08895571B2
Reaction notes
Loading…