Carbon tetrabromide → Tert-butyl (1-bromo-4-methylpentan-2-yl)carbamate

HRID 1646532Notes

Reaction equation

HRID 1646532 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:12][CH2:13][CH3:14])CO)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[C:16]([Br:19])(Br)Br.[C:20]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:12][CH:13]([CH3:14])[CH3:20])[CH2:16][Br:19])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 13969853N-Boc-DL-2-amino-1-pentanol

Product 1

HCID 19107596Tert-butyl (1-bromo-4-methylpentan-2-yl)carbamateYield 68.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of N-tert-butoxycarbonyl-2-aminopentan-1-ol (2.0 g, 9.2 mmol) in dry DCM (30 ml) at 0° C. was treated with tetrabromomethane (6.1 g, 18.4 mmol) followed by triphenylphosphine (4.84 g, 18.4 mmol). The clear reaction mixture immediately changed to yellow. After 30 min. the solvent was removed under reduced pressure and the residue was purified by column chromatography (flash silica gel; 0-40% ethyl acetate in hexane) to give N-tert-butoxycarbonyl-1-bromo-2-amino-4-methylpentane (1.76 g, 68%) as a colourless oil.

Workup

  1. customAfter 30 min. the solvent was removed under reduced pressure
  2. customthe residue was purified by column chromatography (flash silica gel; 0-40% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-2d3d8ecc6a8542f0950869f697db6d58
Source dataset
uspto-grants-1993_01
Patent number
US05180723

Reaction notes

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