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

HRID 1044854노트

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HRID 1044854 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
0 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-31edcb9c8c004d228995a8293ec78fdf
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08563717B2

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