(S)-tert-butyl 2-(5-amino-2-(isopropylsulfonyl)phenyl)pyrrolidine-1-carboxylate → (S)-Methyl(4-(isopropylsulfonyl)-3-(pyrrolidin-2-yl)phenyl)carbamate hydrochloride

HRID 1438128Notes

Reaction equation

HRID 1438128 reaction equation
NC1C=CC(S(C(C)C)(=O)=O)=C([C@@H]2CCCN2C(OC(C)(C)C)=O)C=1.[ClH:26].[CH3:27][N:28]([C:32]1[CH:37]=[CH:36][C:35]([S:38]([CH:41]([CH3:43])[CH3:42])(=[O:40])=[O:39])=[C:34]([C@H:44]2[CH2:48][CH2:47][CH2:46][NH:45]2)[CH:33]=1)[C:29](=[O:31])[OH:30]>>[ClH:26].[CH3:27][N:28]([C:32]1[CH:37]=[CH:36][C:35]([S:38]([CH:41]([CH3:43])[CH3:42])(=[O:40])=[O:39])=[C:34]([C@@H:44]2[CH2:48][CH2:47][CH2:46][NH:45]2)[CH:33]=1)[C:29](=[O:30])[OH:31]

Participants

3

Reactant 2

HCID 57942797(S)-tert-butyl 2-(5-amino-2-(isopropylsulfonyl)phenyl)pyrrolidine-1-carboxylateHCID 67440170(R)-Methyl(4-(isopropylsulfonyl)-3-(pyrrolidin-2-yl)phenyl)carbamate hydrochloride

Product 1

HCID 69007781(S)-Methyl(4-(isopropylsulfonyl)-3-(pyrrolidin-2-yl)phenyl)carbamate hydrochloride

Procedure

44B was prepared from 40B following a procedure similar to that used in the preparation of 44A. 1H NMR (400 MHz, Methanol-d4) δ ppm 1.24 (d, J=6.85 Hz, 3H) 1.35 (d, J=6.85 Hz, 3H) 2.14-2.29 (m, 1H) 2.29-2.45 (m, 2H) 2.45-2.62 (m, 1H) 3.36-3.56 (m, 3H) 3.79 (s, 3H) 7.68 (dd, J=8.56, 1.96 Hz, 1H) 7.95 (d, J=8.56 Hz, 1H) 8.08 (d, J=2.20 Hz, 1H) 8.10-8.19 (m, 2H) 8.60-8.77 (m, 1H) 8.89 (d, J=5.14 Hz, 2H) 9.96 (s, 1H).

Sources & evidence

ORD record
ord-96deedad363e4154a31638d74a9f7416
Source dataset
uspto-grants-2009_11
Patent number
US07622585B2

Reaction notes

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