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

HRID 60241

反応式

HRID 60241 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒2 回

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-21ed99da9d1943258608cfc03367be3a
出典データセット
uspto-grants-2016_09
特許番号
US09440976B2

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