tert-butyl (2S)-2-formylpyrrolidine-1-carboxylate → HCID 58714313, compound
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([N:12]2[CH2:17][CH2:16][N:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[NH:24][S:25]([CH3:28])(=[O:27])=[O:26])[CH2:14][CH2:13]2)=[O:11])=[CH:4][CH:3]=1.OC(C(F)(F)F)=O.N[C@H](CC1C=CC(Cl)=CC=1)C(N1C[CH2:44][N:43]([C:46]2[CH:51]=[CH:50]C=C[C:47]=2[NH:52]S(C)(=O)=O)CC1)=O.C(N1CCC[C@H]1C=O)(OC(C)(C)C)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>>[NH:43]1[CH2:44][CH2:50][CH2:51][C@@H:46]1[CH2:47][NH:52][C@H:9]([CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[C:10]([N:12]1[CH2:17][CH2:16][N:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[NH:24][S:25]([CH3:28])(=[O:27])=[O:26])[CH2:14][CH2:13]1)=[O:11]Participants
5
Procedure
Following the procedure of Example 38, Step 3, (2R)-2-{[(2R)-pyrrolidin-2-yl)methyl]amino}-3-(4-chlorophenyl)-1-(4-{2-[(methylsulfonyl)amino]phenyl}piperazinyl)propan-1-one was prepared from (2R)-2-amino-3-(4-chlorophenyl)-1-(4-{2-[(methylsulfonyl)-amino]phenyl}piperazinyl)propan-1-one TFA salt (0.6 g, 1.1 mmol) in ClCH2Cl2Cl (10 mL), N-Boc-L-prolinal (Aldrich) (280 mg, 1.4 mmol), and NaBH(OAc)3 (Aldrich) (340 mg , 1.9 mmol). The desired compound (TFA salt) was purified by preparative TLC (60% Hexane, 38% CH2Cl2 and 2% 2N NH3 in MeOH), followed by preparative HPLC (TFA buffer) yielding a white solid (14.8 mg). MS (ESI, pos. ion) m/z: 520 (M+H); MS (ESI, neg. ion) m/z: 518 (M−H). Calc'd for C25H34ClN5O3S: 519.21.
Workup
- customThe desired compound (TFA salt) was purified by preparative TLC (60% Hexane, 38% CH2Cl2 and 2% 2N NH3 in MeOH)
Sources & evidence
- ORD record
- ord-51430b97740c42ff9ad60503ea864cd5
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07115607B2
Reaction notes
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