Methanol → HCID 12347985, compound

HRID 2183454Notes

Reaction equation

HRID 2183454 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([O:16]C)[CH:11]=1)[CH3:9])(C)(C)C.B(Br)(Br)Br.CO>C(Cl)Cl>[NH2:7][C@H:8]([C:10]1[CH:11]=[C:12]([OH:16])[CH:13]=[CH:14][CH:15]=1)[CH3:9]

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 56971803HCID 56971803, compound

Product 1

HCID 12347985HCID 12347985, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-[1-(3-Methoxy-phenyl)-ethyl]-carbamic acid tert-butyl ester (50.2 g, 210 mmol) in CH2Cl2 (500 mL) was cooled to −78° C. Boron tribromide (450 mL, 1.0M in CH2Cl2) was added slowly and the resulting mixture was warmed to room temperature and stirred for 3 h. The reaction mixture was again cooled to 0° C. and methanol (500 mL) was added slowly. The solvent was removed in vacuo, and the residue was purified by flash column chromatography on silica gel eluting with 5% MeOH in EtOAc to give the title product in quantitative yield.

Workup

  1. temperatureThe reaction mixture was again cooled to 0° C.
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified by flash column chromatography on silica gel eluting with 5% MeOH in EtOAc

Sources & evidence

ORD record
ord-45190bc35cd744dca4f87ca6903462eb
Source dataset
uspto-grants-2005_05
Patent number
US06900210B2

Reaction notes

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