Boron tribromide → HCID 12347985, compound

HRID 2307417Notes

Reaction equation

HRID 2307417 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>ClCCl>[NH2:7][C@H:8]([C:10]1[CH:11]=[C:12]([OH:16])[CH:13]=[CH:14][CH:15]=1)[CH3:9]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 56971803HCID 56971803, compound

Product 1

HCID 12347985HCID 12347985, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [(S)-1-(3-methoxyphenyl)ethyl]carbamic acid tert-butyl ester (3 g, 12 mmol) in dichloromethane (25 mL) at −78° C. was added BBr3 (1.0 M solution in dichloromethane) (26 mL, 26 mmol) dropwise. After the addition, the solution was warmed up to room temperature. The reaction mixture was quenched with methanol (100 mL) and concentrated under vacuum. This process was repeated until no white fumes were observed upon adding methanol. The title compound was obtained as pale yellow solid (2.6 g, quantitative yield). The crude product was used without any further purification

Workup

  1. additionAfter the addition
  2. customThe reaction mixture was quenched with methanol (100 mL)
  3. concentrationconcentrated under vacuum
  4. additionupon adding methanol

Sources & evidence

ORD record
ord-17e288eba23743cdbdb851ff6da6d1eb
Source dataset
uspto-grants-2004_12
Patent number
US06831080B2

Reaction notes

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