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Acetic Acid → (2S)-2-(1,1-dioxidoisothiazolidin-2-yl)-4-methyl-N-{(3aS,4R,6aR)-2-[3-(trifluoromethyl)benzyl]octahydrocyclopenta[c]pyrrol-4-yl}pentanamide

HRID 1092620
Notes
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Reaction equation

HRID 1092620 reaction equation
[O:1]=[S:2]1(=[O:23])[CH2:6][CH2:5][CH2:4][N:3]1[C@@H:7]([CH2:19][CH:20]([CH3:22])[CH3:21])[C:8]([NH:10][C@H:11]1[C@H:18]2[C@H:14]([CH2:15][NH:16][CH2:17]2)[CH2:13][CH2:12]1)=[O:9].[F:24][C:25]([F:35])([F:34])[C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][CH:33]=1)[CH:29]=O.C(O)(=O)C.C([BH3-])#N>ClCCl>[O:23]=[S:2]1(=[O:1])[CH2:6][CH2:5][CH2:4][N:3]1[C@@H:7]([CH2:19][CH:20]([CH3:21])[CH3:22])[C:8]([NH:10][C@H:11]1[C@H:18]2[C@H:14]([CH2:15][N:16]([CH2:29][C:28]3[CH:31]=[CH:32][CH:33]=[C:26]([C:25]([F:24])([F:34])[F:35])[CH:27]=3)[CH2:17]2)[CH2:13][CH2:12]1)=[O:9]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 679903-(Trifluoromethyl)benzaldehydeHCID 498716Cyano-borohydrideHCID 66590695(2S)-2-(1,1-dioxidoisothiazolidin-2-yl)-4-methyl-N-[(3aS,4R,6aR)-octahydrocyclopenta[c]pyrrol-4-yl]pentanamide

Product 1

HCID 66590670(2S)-2-(1,1-dioxidoisothiazolidin-2-yl)-4-methyl-N-{(3aS,4R,6aR)-2-[3-(trifluoromethyl)benzyl]octahydrocyclopenta[c]pyrrol-4-yl}pentanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2S)-2-(1,1-Dioxidoisothiazolidin-2-yl)-4-methyl-N-[(3aS,4R,6aR)-octahydrocyclopenta[c]pyrrol-4-yl]pentanamide (204 mg, 0.594 mmol) and 3-(trifluoromethyl)benzaldehyde (0.158 mL, 1.188 mmol) were dissolved in dichloromethane (3 mL). Acetic acid (1 mL) was added. The reaction was stirred at ambient temperature for 20 min, then PS-cyanoborohydride (487 mg, 1.188 mmol) was added. The reaction was stirred at room temperature overnight, then filtered, and the solvent was removed in vacuo. The crude material was purified by silica gel chromatography using 1-10% methanol (2 N ammonia)/dichloromethane to the title compound: 1H NMR (500 MHz, pyridine-d5) δ ppm 8.79 (d, J=7.0, 1H), 7.75 (d, J=10.3, 1H), 7.61-7.54 (m, 2H), 7.44 (t, J=7.7, 1H), 4.52 (dd, J=6.6, 8.9, 1H), 4.38 (dq, J=6.4, 12.6, 1H), 3.94 (dd, J=7.3, 16.2, 1H), 3.57 (dd, J=9.1, 13.5, 1H), 3.50-3.37 (m, 2H), 3.31-3.19 (m, 2H), 2.79 (ddd, J=3.0, 9.1, 19.0, 1H), 2.62-2.54 (m, 1H), 2.54-2.45 (m, 1H), 2.43-2.36 (m, 1H), 2.31-2.16 (m, 4H), 2.13-2.03 (m, 1H), 1.94-1.78 (m, 3H), 1.77-1.59 (m, 2H), 1.39 (dt, J=6.5, 19.8, 1H), 0.88 (d, J=6.6, 3H), 0.82 (dd, J=2.3, 6.5, 3H); MS (ESI+) m/z 502 (M+H)+.

Workup

  1. stirringThe reaction was stirred at room temperature overnight
  2. filtrationfiltered
  3. customthe solvent was removed in vacuo
  4. customThe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-e28b3987e6c5423a93bd5228947d762b
Source dataset
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08129417B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes