(S)-3-(Toluene-4-sulfonyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester → (2R,3'R)-2-Methyl-[1,3]bipyrrolidinyl-1'-carboxylic acid tert-butyl ester

HRID 1911071Notes

Reaction equation

HRID 1911071 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@H:10]([N:13]2[CH2:17][CH2:16][CH2:15][C@H:14]2[CH3:18])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(OC(N1CC[C@H](OS(C2C=CC(C)=CC=2)(=O)=O)C1)=O)(C)(C)C>>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([N:13]2[CH2:17][CH2:16][CH2:15][C@H:14]2[CH3:18])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 57957824(S)-3-(Toluene-4-sulfonyloxy)-pyrrolidine-1-carboxylic acid tert-butyl esterHCID 59401895(2R,3'S)-2-Methyl-[1,3]bipyrrolidinyl-1'-carboxylic acid tert-butyl ester

Product 1

HCID 59401893(2R,3'R)-2-Methyl-[1,3]bipyrrolidinyl-1'-carboxylic acid tert-butyl ester

Procedure

The title compound was prepared in a manner substantially the same as intermediate (2R,3′S)-2-Methyl-[1,3′]bipyrrolidinyl-1′-carboxylic acid tert-butyl ester by condensing 3-(3S)-(toluene-4-sulfonyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester and R-(−)-2-methylpiperindine (obtained from Advanced Asymmetrics). LCMS: RT=1.09 minutes, MS: 255 (M+H).

Sources & evidence

ORD record
ord-ba3d14b8d76b42ca8b86e2c68c0d1b18
Source dataset
uspto-grants-2013_12
Patent number
US08604046B2

Reaction notes

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