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

HRID 1460477Notes

Reaction equation

HRID 1460477 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-439af09006414e7db27e9e5dabc8d6d9
Source dataset
uspto-grants-1991_12
Patent number
US05071844

Reaction notes

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