rac-{(3R,4S)-4-(3,4-Dichloro-phenyl)-1-[1-(1-methyl-cyclopropanecarbonyl)-piperidine-4-carbonyl]-pyrrolidin-3-yl}-methyl-carbamic acid tert-butyl ester → [(3R,4S)-3-(3,4-Dichloro-phenyl)-4-methylamino-pyrrolidin-1-yl]-[1-(1-methyl-cyclopropanecarbonyl)-piperidin-4-yl]-methanone
Reaction equation
C(OC(=O)N([C@H]1[C@H](C2C=CC(Cl)=C(Cl)C=2)CN(CC2C=CC=CC=2)C1)C)(C)(C)C.C(O[C:35](=O)[N:36]([C@@H:38]1[C@@H:42]([C:43]2[CH:48]=[CH:47][C:46]([Cl:49])=[C:45]([Cl:50])[CH:44]=2)[CH2:41][N:40]([C:51]([CH:53]2[CH2:58][CH2:57][N:56]([C:59]([C:61]3([CH3:64])[CH2:63][CH2:62]3)=[O:60])[CH2:55][CH2:54]2)=[O:52])[CH2:39]1)C)(C)(C)C>>[Cl:50][C:45]1[CH:44]=[C:43]([C@H:42]2[C@H:38]([NH:36][CH3:35])[CH2:39][N:40]([C:51]([CH:53]3[CH2:58][CH2:57][N:56]([C:59]([C:61]4([CH3:64])[CH2:62][CH2:63]4)=[O:60])[CH2:55][CH2:54]3)=[O:52])[CH2:41]2)[CH:48]=[CH:47][C:46]=1[Cl:49]Participants
Reactant 2
Product 1
Procedure
In analogy to the procedure described for the synthesis of rac-[(3R,4S)-4-(3,4-Dichloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid tert-butyl ester (example 1, e) the title compound was prepared from [(3S,4R)-1-Benzyl-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid tert-butyl ester through cleavage of the benzyl group. And, in analogy to the procedure described for the synthesis of rac-{(3R,4S)-4-(3,4-Dichloro-phenyl)-1-[1-(1-methyl-cyclopropanecarbonyl)-piperidine-4-carbonyl]-pyrrolidin-3-yl}-methyl-carbamic acid tert-butyl ester (example 1, f) the Boc-protected title compound was prepared from the intermediately built [(3S,4R)-4-(3,4-Dichloro-phenyl)-pyrrolidin-3-yl]-methyl-carbamic acid tert-butyl ester and 1-(1-Methyl-cyclopropanecarbonyl)-piperidine-4-carboxylic acid. The title compound was subsequently isolated after acidic cleavage of the Boc group with TFA. MS m/e: 438.1 [M+H]+.
Sources & evidence
- ORD record
- ord-12bba89005a64f0499a023e5eaaad362
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09226916B2
Reaction notes
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