Acetic Acid → tert-Butyl 4-hydroxy-[1,4'-bipiperidine]-1'-carboxylate

HRID 245138

반응식

HRID 245138 반응식
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[NH:15]1[CH2:20][CH2:19][CH:18]([OH:21])[CH2:17][CH2:16]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[OH:21][CH:18]1[CH2:19][CH2:20][N:15]([CH:2]2[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]2)[CH2:16][CH2:17]1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 79341Piperidin-4-olHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 9835508tert-Butyl 4-hydroxy-[1,4'-bipiperidine]-1'-carboxylate수율 39.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A mixture of 1,1-dimethylethyl 4-oxo-1-piperidinecarboxylate (3.15 g, 15.8 mmol), 4-piperidinol (1.0 g, 9.88 mmol), and acetic acid (0.8 mL) in methylene chloride (30 mL) was stirred for 3 h at room temperature. Sodium triacetoxyborohydride (3.35 g, 15.8 mmol) was added and the mixture was stirred at room temperature for 18 h. The solvent was removed under reduced pressure, and the residue was dissolved in methylene chloride and washed with 1N HCl. The aqueous phase was extracted with ether (3×10 mL) and adjusted to pH 9-10 with 1N NaOH. The basic aqueous mixture was extracted with methylene chloride (3×10 mL). The combined organic extracts were concentrated in vacuo to afford 1,1-dimethylethyl 4-hydroxy-1,4′-bipiperidine-1′-carboxylate (1.1 g, 39% yield). This material was used in the next step without further purification.

후처리

  1. stirringthe mixture was stirred at room temperature for 18 h
  2. customThe solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in methylene chloride
  4. washwashed with 1N HCl
  5. extractionThe aqueous phase was extracted with ether (3×10 mL)
  6. extractionThe basic aqueous mixture was extracted with methylene chloride (3×10 mL)
  7. concentrationThe combined organic extracts were concentrated in vacuo

출처 및 근거

ORD 기록
ord-132a556132594849b5222303bbdd35e9
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658636B2

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