4-Phenylpiperidine → 1-Benzyl-3-(RS)-(4-phenylpiperidinylmethyl)-4-(RS)-(3-thienyl)pyrrolidine

HRID 380464ノート

反応式

HRID 380464 の反応式
[CH2:1]([N:8]1[CH2:12][CH:11]([C:13]2[CH:17]=[CH:16][S:15][CH:14]=2)[CH:10]([CH:18]=O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]1([CH:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C.CCN(CC)CC>[CH2:1]([N:8]1[CH2:12][CH:11]([C:13]2[CH:17]=[CH:16][S:15][CH:14]=2)[CH:10]([CH2:18][N:29]2[CH2:30][CH2:31][CH:26]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:27][CH2:28]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

6

反応物 3

HCID 698734-PhenylpiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 183647191-Benzyl-3-(SR)-formyl-4-(RS)-(3-thienyl)pyrrolidine

生成物 1

HCID 99537311-Benzyl-3-(RS)-(4-phenylpiperidinylmethyl)-4-(RS)-(3-thienyl)pyrrolidine収率 115%

試薬・触媒・溶媒 2

HCID 63651,1-Dichloroethane溶媒HCID 8471Triethylamine溶媒

実験手順

To a solution of 0.13 g (0.48 mmol) of 1-benzyl-3-(SR)-formyl-4-(RS)-(3-thienyl)pyrrolidine and 0.13 g (0.67 mmol) of 4-phenylpiperidine in 2 mL of dichloroethane and 0.1 mL of Et3N at rt was added 0.21 g (0.96 mmol) of sodium triacetoxyborohydride. After stirring for 3 h at rt, the reaction mixture was partitioned between CH2Cl2 and sat'd NaHCO3. The organic fraction was dried over Na2SO4, filtered and the filtrate was concentrated. The residue was purified by chomatography (silica, acetone: hexanes, 1:3) to give 0.23 g of the title compound. 1H NMR CDCl3) δ7.21-7.44 (m, 11H), 7.07-7.13 (m, 2H), 3.74 (d, 1H, J=12.8 Hz), 3.67 (d, 1H, J=13.1 Hz). Mass Spectrum (CI) m/e=417 (M+1).

後処理

  1. customthe reaction mixture was partitioned between CH2Cl2
  2. dry with materialThe organic fraction was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by chomatography (silica, acetone: hexanes, 1:3)

出典と根拠

ORDレコード
ord-517a83f4c7a64873b438aa4ac63b579e
出典データセット
uspto-grants-2001_10
特許番号
US06303593B1

反応ノート

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