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Benzyl chloroformate → (S)-1-Boc-3-(Cbz-amino-methyl)-piperidine

HRID 963286
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HRID 963286 반응식
[OH-].[Na+].[NH2:3][CH2:4][C@@H:5]1[CH2:10][CH2:9][CH2:8][N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6]1.Cl[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.CCCCCC.O>[CH2:22]([O:21][C:19]([NH:3][CH2:4][C@@H:5]1[CH2:10][CH2:9][CH2:8][N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6]1)=[O:20])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 1502022tert-Butyl (3S)-3-(aminomethyl)piperidine-1-carboxylate

생성물 1

HCID 45158795(S)-1-Boc-3-(Cbz-amino-methyl)-piperidine

시약·촉매·용매 3

HCID 94433Tetrabutylammonium hydrogen sulfate촉매HCID 962
Water
용매
HCID 8058Hexane용매

실험 절차

A)a) 3.7 g of tetrabutylammonium hydrogen sulphate and 100 ml of 1N sodium hydroxide solution are added to a solution of 10.0 g of t-butyl (S)-3-aminomethyl-1-piperidinecarboxylate (Example 6d) in 400 ml of hexane and 100 ml of water. 9.3 ml of benzyl chloroformate are added dropwise to this mixture and the mixture obtained is stirred at room temperature for 3 hours. Subsequently, the organic phase is separated, washed with water, 10% citric acid, water and saturated sodium bicarbonate solution, dried and evaporated. t-Butyl (S)-3-[(1-(benzyloxy)formamido]-methyl]-1-piperidinecarboxylate is obtained.

후처리

  1. customthe mixture obtained
  2. customSubsequently, the organic phase is separated
  3. washwashed with water, 10% citric acid, water and saturated sodium bicarbonate solution
  4. customdried
  5. customevaporated

출처 및 근거

ORD 기록
ord-019b3b71bc7b4bf2a6fc8d79937d4430
출처 데이터셋
uspto-grants-1998_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05763436

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