Beta-Propiolactone → tert-Butyl 1-(oxetan-3-yl)piperidin-4-yl carbamate

HRID 60241

반응식

HRID 60241 반응식
[C:1]([O:5][C:6](=[O:14])[NH:7][CH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[O:15]1[CH2:18][CH2:17][C:16]1=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[C:1]([O:5][C:6](=[O:14])[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([CH:17]2[CH2:18][O:15][CH2:16]2)[CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 2365Beta-PropiolactoneHCID 7238334-(N-Boc-amino)piperidineHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 56604528tert-Butyl 1-(oxetan-3-yl)piperidin-4-yl carbamate수율 67%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매2회

실험 절차

To a suspension of piperidin-4-yl-carbamic acid tert-butyl ester (200 mg, 1.0 mmol) in DCE (6 mL) was added oxetanone (60 mg, 0.83 mmol) in DCE (2 mL). After 75 min, sodium triacetoxyborohydride (282 mg, 1.33 mmol) was added in one portion. After 20 hours at ambient temperature, the reaction mixture was loaded directly onto a 5 g SCX-2 cartridge which was washed with methanol, then 2N ammonia in methanol. Concentration of the combined basic fractions in-vacuo followed by flash chromatography of the resultant residue (silica, 5 g column, Si-SPE, 0-10% methanol in dichloromethane) afforded the title compound as a white solid (141 mg, 67%). 1H NMR (300 MHz, CDCl3): 4.62-4.61 (m, 4H), 4.44 (s, 1H), 3.46-3.45 (m, 2H), 2.67 (d, J=10.9 Hz, 2H), 2.02-1.88 (m, 4H), 1.44 (s, 9H).

후처리

  1. waitAfter 20 hours at ambient temperature
  2. washwas washed with methanol

출처 및 근거

ORD 기록
ord-21ed99da9d1943258608cfc03367be3a
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440976B2

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