Benzyl chloroformate → Benzyl 4-(hydroxymethyl)piperidine-1-carboxylate

HRID 278218

반응식

HRID 278218 반응식
CCN(C(C)C)C(C)C.[OH:10][CH2:11][CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.Cl[C:19]([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20]>C(Cl)Cl.C(OCC)(=O)C>[CH2:22]([O:21][C:19]([N:15]1[CH2:16][CH2:17][CH:12]([CH2:11][OH:10])[CH2:13][CH2:14]1)=[O:20])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

참가 물질

6

반응물 3

HCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 4207714-Piperidinemethanol

생성물 1

HCID 736490Benzyl 4-(hydroxymethyl)piperidine-1-carboxylate수율 95.4%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

DIPEA (4.6 mL, 3.4 g, 26 mmol) was added to a solution of 4-(hydroxymethyl)piperidine (2.00 g, 17.4 mmol) dissolved in methylene chloride (20 mL). The solution was cooled in an ice bath and benzyl chloroformate (2.5 mL, 3.0 g, 18 mmol) was added dropwise over 10 min. After warming to rt and stirring for 96 h, the mixture was diluted with ethyl acetate (50 mL) and washed in succession with 25 mL each of saturated aq. sodium bicarbonate, 2N aq. HCl, saturated aq. sodium bicarbonate, and saturated aq. brine. The organic layer was dried (sodium sulfate), decanted, and evaporated to give 4.14 g of 1-(benzyloxycarbonyl)-4-(hydroxymethyl)piperidine.

후처리

  1. temperatureThe solution was cooled in an ice bath
  2. washwashed in succession with 25 mL each of saturated aq. sodium bicarbonate, 2N aq. HCl, saturated aq. sodium bicarbonate, and saturated aq. brine
  3. dry with materialThe organic layer was dried (sodium sulfate)
  4. customdecanted
  5. customevaporated

출처 및 근거

ORD 기록
ord-7b25dbd6635246aea9e80cbaff47567b
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06358979B1

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