Water → tert-Butyl 4-(3-hydroxypropyl)tetrahydro-1(2h)-pyridinecarboxylate

HRID 220895노트

반응식

HRID 220895 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][C:16](O)=[O:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].B.O>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][CH2:16][OH:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 962WaterHCID 6331BoraneHCID 15125403-(1-((Tert-butoxy)carbonyl)piperidin-4-yl)propanoic acid

생성물 1

HCID 2800739tert-Butyl 4-(3-hydroxypropyl)tetrahydro-1(2h)-pyridinecarboxylate수율 99%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

4-(2-Carboxy-ethyl)-piperidine-1-carboxylic acid tert-butyl ester (1.0 g, 3.9 mmol, according to the procedure described in J. Med. Chem., 41(14), 2492, 1998) was dissolved in THF (50 ml) and cooled down to 0° C. 2M Borane solution in THF (3.9 ml, 7.8 mmol) was added slowly and the mixture was stirred for 20 h at room temperature. Water was added and solvents were concentrated in vacuo. The residue was dissolved in EtOAC, basified with NaHCO3, washed with brine, dried and concentrated in vacuo to yield the title compound (938 mg, 99%).

후처리

  1. concentrationsolvents were concentrated in vacuo
  2. dissolutionThe residue was dissolved in EtOAC
  3. washwashed with brine
  4. customdried
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-96f953d2d88b4bf29ee9ca51866ad082
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08202858B2

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