Hydrochloric Acid → (R)-2-(4-Phenoxy-phenylsulfanylmethyl)-pyrrolidine

HRID 1909665Notes

Reaction equation

HRID 1909665 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][S:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[CH:17][CH:16]=1)=O)(C)(C)C.Cl>CO.C(OCC)C>[O:21]([C:18]1[CH:19]=[CH:20][C:15]([S:14][CH2:13][C@H:9]2[CH2:10][CH2:11][CH2:12][NH:8]2)=[CH:16][CH:17]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68997777(R)-2-(4-Phenoxy-phenylsulfanylmethyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 59753059(R)-2-(4-Phenoxy-phenylsulfanylmethyl)-pyrrolidineYield 94%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To the product from step 1 (272 mg, 0.705 mmol) in methanol (3 mL) was added 2M HCl in diethyl ether (12 mL) and the resulting mixture was stirred at rt for 6 h. The solvent was removed in vacuo to obtain the title product as a solid (135 mg, 94%); MS; m/z 286 (M+H); LCMS (UV) 99%. 1H NMR (400 MHz, CD3OD) δ 1.73-1.81 (m, 1H), 2.0-2.11 (m, 2H), 2.21-2.27 (m, 1H), 3.08-3.13 (m, 2H), 3.26-3.36 (m, 2H), 3.61-3.64 (m, 1H), 7.50 (d, 2H, J=11.6 Hz), 7.35-7.39 (m, 2H), 7.15 (t, 1H, J=16 Hz); 6.96-7.01 (m, 4H)

Workup

  1. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-1238da53f0114ec88060338304036223
Source dataset
uspto-grants-2013_12
Patent number
US08598359B2

Reaction notes

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