1,2-Ethanedithiol → 2-(2-(1-(Benzyloxycarbonyl)piperidin-4-yl)ethyl)-2-phenyl-1,3-dithiolane

HRID 1386768ノート

反応式

HRID 1386768 の反応式
B(F)(F)F.C(O)(=O)C.[CH2:9]([SH:12])[CH2:10][SH:11].[CH2:13]([O:20][C:21]([N:23]1[CH2:28][CH2:27][CH:26]([CH2:29][CH2:30][C:31](=O)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:25][CH2:24]1)=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(Cl)Cl.CCOCC>[CH2:13]([O:20][C:21]([N:23]1[CH2:28][CH2:27][CH:26]([CH2:29][CH2:30][C:31]2([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[S:12][CH2:9][CH2:10][S:11]2)[CH2:25][CH2:24]1)=[O:22])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

参加物

6

反応物 3

HCID 109021,2-EthanedithiolHCID 61423Hydrogen (acetato-O)trifluoroborate(1-)HCID 181874541-(Benzyloxycarbonyl)-4-(3-oxo-3-phenylpropyl)piperidine

生成物 1

HCID 181877152-(2-(1-(Benzyloxycarbonyl)piperidin-4-yl)ethyl)-2-phenyl-1,3-dithiolane収率 92.7%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒

実験手順

Boron trifluoride-acetic acid complex (BF3.2CH3CO2H, 0.370 mL, 501 mg, 2.67 mmol) was added to a solution of 1,2-ethanedithiol (0.440 mL, 494 mg, 5.25 mmol) and (1-(benzyloxycarbonyl)-4-(3-oxo-3-phenylpropyl)piperidine (930 mg, 2.65 mmol) in CH2Cl2 (4.0 mL) at RT. After 6 h, the mixture was diluted with ether (50 mL) and washed with saturated aq. NaHCO3 (2×25 mL), 2.5 N NaOH (25 mL), and saturated aq. NaCl (25 mL). The organic layer was dried (Na2SO4), decanted, and evaporated. The crude product was purified by flash column chromatography on silica gel eluting with 9:1 v/v hexanes/EtOAc to give 1.05 g of the title compound as a colorless liquid: 1H NMR (400 MHz) S 7.66 (d, J=8, 2H), 7.38-7.26 (m, 7H), 7.22 (t, J=8), 1H), 5.10 (s, 2H), 4.18-4.02 (m, 2H), 3.41-3.32 (m, 2H), 3.29-3.20 (m, 2H), 2.79-2.62 (m, 2H), 2.40-2.32 (m, 2H), 1.65-1.54 (m, 2H), 1.40-1.27 (m, 1H), 1.24-1.16 (m, 2H), 1.10-0.97 (m, 2H); ESI-MS 428 (M+H); HPLC A: 4.21 min.

後処理

  1. customat RT
  2. washwashed with saturated aq. NaHCO3 (2×25 mL), 2.5 N NaOH (25 mL), and saturated aq. NaCl (25 mL)
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. customdecanted
  5. customevaporated
  6. customThe crude product was purified by flash column chromatography on silica gel eluting with 9:1 v/v hexanes/EtOAc

出典と根拠

ORDレコード
ord-4574a55d742c4640b59651070545223f
出典データセット
uspto-grants-2001_07
特許番号
US06265434B1

反応ノート

読み込み中…