Methanol → Tert-butyl 3-(3-chlorophenyl)-3-hydroxypropyl(methyl)carbamate

HRID 426034Notes

Reaction equation

HRID 426034 reaction equation
S(C)C.[Cl:4][C:5]1[CH:6]=[C:7]([C:11](=[O:23])[CH2:12][CH2:13][N:14]([CH3:22])[C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH:8]=[CH:9][CH:10]=1.CO>C1COCC1>[Cl:4][C:5]1[CH:6]=[C:7]([CH:11]([OH:23])[CH2:12][CH2:13][N:14]([CH3:22])[C:15](=[O:21])[O:16][C:17]([CH3:18])([CH3:19])[CH3:20])[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 1068Dimethyl SulfideHCID 59364354Tert-butyl 3-(3-chlorophenyl)-3-oxopropyl(methyl)carbamate

Product 1

HCID 59364384Tert-butyl 3-(3-chlorophenyl)-3-hydroxypropyl(methyl)carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution R—CBS (20.2 mL, 20.2 mmol) and BH3.Me2S (30.3 mL, 303 mmol) in THF (250 mL) was added a solution of tert-butyl 3-(3-chlorophenyl)-3-oxopropyl(methyl)carbamate (60 g, 0.202 mol) in THF (300 mL) at −15° C. After addition, the mixture was stirred at room temperature for 1 hour. Methanol was added drop wise carefully at −15° C. The solvent was removed under reduced pressure, the residue was purified by column chromatography on silica gel eluting with AcOEt/petroleum ether (1:15→1:8) to provide the light yellow oil. 1H NMR (CDCl3, 400 MHz) δ 1.49 (s, 9H), 1.70 (m, 1H), 1.94 (m, 1H), 2.87 (s, 3H), 3.01 (m, 1H), 3.96 (m, 1H), 4.52 (m, 1H), 7.26 (m, 4H).

Workup

  1. additionAfter addition
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was purified by column chromatography on silica gel eluting with AcOEt/petroleum ether (1:15→1:8)
  4. customto provide the light yellow oil

Sources & evidence

ORD record
ord-dc307731f179458c9c8854d8cd0ebf6b
Source dataset
uspto-grants-2012_01
Patent number
US08106221B2

Reaction notes

Loading…