Chloroacetyl chloride → Tert-butyl 4-[benzyl(chloroacetyl)amino]-3-hydroxypiperidine-1-carboxylate

HRID 1852720노트

반응식

HRID 1852720 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:10]([OH:22])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC(N1CCC(O)C(NCC2C=CC=CC=2)C1)=O)(C)(C)C.C(N(CC)CC)C.[Cl:52][CH2:53][C:54](Cl)=[O:55]>C(Cl)Cl>[CH2:15]([N:14]([C:54](=[O:55])[CH2:53][Cl:52])[CH:11]1[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9][CH:10]1[OH:22])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

참가 물질

6

반응물 4

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 57452747Tert-butyl-4-(benzylamino)-3-hydroxypiperidine-1-carboxylateHCID 57452748Tert-butyl-3-(benzylamino)-4-hydroxypiperidine-1-carboxylate

생성물 1

HCID 86724481Tert-butyl 4-[benzyl(chloroacetyl)amino]-3-hydroxypiperidine-1-carboxylate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of tert-butyl-4-(benzylamino)-3-hydroxypiperidine-1-carboxylate and tert-butyl-3-(benzylamino)-4-hydroxypiperidine-1-carboxylate (153 g, 0.42 mol, crude) and triethylamine (126 g, 1.25 mol) in DCM (800 mL) was added drop wise chloroacetyl chloride (33 g, 0.45 mol) at room temperature. The mixture was stirred at room temperature overnight. The mixture was quenched with water (300 mL) at 0° C., and extracted with DCM (500 mL×3). The organic layer was washed with brine (1 L), dried over sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography to afford tert-butyl 4-[benzyl(chloroacetyl)amino]-3-hydroxypiperidine-1-carboxylate as a mixture of trans diastereomers which was used directly in the next step.

후처리

  1. customThe mixture was quenched with water (300 mL) at 0° C.
  2. extractionextracted with DCM (500 mL×3)
  3. washThe organic layer was washed with brine (1 L)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-d5578f7688564f6792865b71a02f8fda
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08962611B2

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