Benzyl chloroformate → (2R)-1-((Benzyloxy)carbonyl)piperidine-2-carboxylic acid

HRID 1954677

반응식

HRID 1954677 반응식
[NH:1]1[CH2:9][CH2:8][CH2:7][CH2:6][C@@H:2]1[C:3]([OH:5])=[O:4].[OH-].[Na+].Cl[C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14]>O1CCCC1.O>[N:1]1([C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])[CH2:9][CH2:8][CH2:7][CH2:6][C@@H:2]1[C:3]([OH:5])=[O:4]

참가 물질

6

반응물 3

HCID 10387Benzyl chloroformateHCID 14798Sodium Hydroxide2회HCID 736316Pipecolic acid, (+)-

생성물 1

HCID 688346(2R)-1-((Benzyloxy)carbonyl)piperidine-2-carboxylic acid수율 95%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

D-hPro-OH (5.0 g, 38.7 mmol) was dissolved in tetrahydrofuran (100 mL) and water (30 mL). The pH of the solution was adjusted to 9.5 with 2N NaOH and benzyl chloroformate (5.5 mL, 38.7 mmol) was added dropwise and the pH maintained at 9.5 with 2N NaOH. The reaction was stirred for an additional 1 hour at room temperature. The organic solvent was evaporated in vacuo, and diethyl ether (100 mL) and water (50 mL) were added to the residue. The aqueous layer was separated, the pH of the aqueous solution was adjusted to 2.8 with 3N HCl, and ethyl acetate (150 mL) was added. The organic layer was separated and dried (MgSO4) and the filtrate was concentrated in vacuo to give 9.6 g (95%) of a clear oil.

후처리

  1. additionwas added dropwise
  2. customThe organic solvent was evaporated in vacuo, and diethyl ether (100 mL) and water (50 mL)
  3. additionwere added to the residue
  4. customThe aqueous layer was separated
  5. additionwas added
  6. customThe organic layer was separated
  7. dry with materialdried (MgSO4)
  8. concentrationthe filtrate was concentrated in vacuo

출처 및 근거

ORD 기록
ord-562908c1f98b4860998d2ec81c0eb866
출처 데이터셋
uspto-grants-2000_09
특허 번호
US06124277

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