Carbon tetrabromide → (R)-Tert-butyl 3-(bromomethyl)piperidine-1-carboxylate

HRID 1044854Notes

Reaction equation

HRID 1044854 reaction equation
Br[C:2]([Br:5])(Br)Br.OC[C@@H:8]1[CH2:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[Br:5][CH2:2][C@@H:12]1[CH2:13][CH2:8][CH2:9][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:11]1

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 1514447tert-butyl (3R)-3-(hydroxymethyl)piperidine-1-carboxylate

Product 1

HCID 40425280(R)-Tert-butyl 3-(bromomethyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Tetrabromomethane (1.23 g) was added to a solution of 1,1-dimethylethyl (3R)-3-(hydroxymethyl)-1-piperidinecarboxylate (500 mg) in methylene chloride (2.7 mL). The reaction mixture was cooled to 0° C. and a solution of triphenylphosphine (731 mg) in methylene chloride (2.7 mL) was slowly added. After 1 hour at 0° C., the reaction mixture was concentrated and directly purified by chromatography on silica gel eluting with heptane/ethyl acetate 1:15 followed 1:10 to yield the title compound as a slightly yellow oil (627 mg).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customdirectly purified by chromatography on silica gel eluting with heptane/ethyl acetate 1:15

Sources & evidence

ORD record
ord-31edcb9c8c004d228995a8293ec78fdf
Source dataset
uspto-grants-2013_10
Patent number
US08563717B2

Reaction notes

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