(-)-Mandelic acid → (S)-5,11-Dihydro-5-[1-(4-methoxyphenethyl)-2-pyrrolidinylmethyl]dibenzo[b,e][1,4]thiazepine (R)-mandelate

HRID 1460477ノート

反応式

HRID 1460477 の反応式
[C:1]([OH:11])(=[O:10])[C@@H:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3].[CH3:12][O:13][C:14]1[CH:42]=[CH:41][C:17]([CH2:18][CH2:19][N:20]2[CH2:24][CH2:23][CH2:22][C@H:21]2[CH2:25][N:26]2[C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=3[CH2:30][S:29][C:28]3[CH:37]=[CH:38][CH:39]=[CH:40][C:27]2=3)=[CH:16][CH:15]=1>ClCCl>[C:1]([OH:11])(=[O:10])[C@@H:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[OH:3].[CH3:12][O:13][C:14]1[CH:15]=[CH:16][C:17]([CH2:18][CH2:19][N:20]2[CH2:24][CH2:23][CH2:22][C@H:21]2[CH2:25][N:26]2[C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=3[CH2:30][S:29][C:28]3[CH:37]=[CH:38][CH:39]=[CH:40][C:27]2=3)=[CH:41][CH:42]=1

参加物

4

反応物 2

HCID 11914(-)-Mandelic acidHCID 9824029(S)-5,11-Dihydro-5-[1-(4-methoxyphenethyl)-2-pyrrolidinylmethyl]dibenzo[b,e][1,4]thiazepine

生成物 1

HCID 131717092(S)-5,11-Dihydro-5-[1-(4-methoxyphenethyl)-2-pyrrolidinylmethyl]dibenzo[b,e][1,4]thiazepine (R)-mandelate収率 83%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A solution of (R)-mandelic acid (88 mg) and (S)-5,11-dihydro-5-[1-(4-methoxyphenethyl)-2-pyrrolidinylmethyl]dibenzo[b,e][1,4]thiazepine (see Examples 1 and 6) (250 mg) in dichloromethane (10 ml) was stirred at room temperature for 16 hours and evaporated under reduced pressure. The residue was triturated with ether and the resulting solid collected, dried and recrystallised from ethyl acetate/hexane to give the title compound as colourless crystals, (250 mg, 83%), m.p. 151°-153° C., [α]58925 -70.4° (c=0.575 in ethanol).

後処理

  1. customevaporated under reduced pressure
  2. customThe residue was triturated with ether
  3. customthe resulting solid collected
  4. customdried
  5. customrecrystallised from ethyl acetate/hexane

出典と根拠

ORDレコード
ord-439af09006414e7db27e9e5dabc8d6d9
出典データセット
uspto-grants-1991_12
特許番号
US05071844

反応ノート

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