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

HRID 2401095Notes

Reaction equation

HRID 2401095 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[C@@H]1CCCN1>>[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

4

Reactant 3

HCID 641544(R)-2-MethylpyrrolidineHCID 23560883(R)-tert-Butyl 3-(tosyloxy)pyrrolidine-1-carboxylateHCID 59401846(2S,3'S)-2-Methyl-[1,3]bipyrrolidinyl-1'-carboxylic acid tert-butyl ester

Product 1

HCID 59401895(2R,3'S)-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 (xi), (2S,3′S)-2-methyl-[1,3′]bipyrrolidinyl-1′-carboxylic acid tert-butyl ester, by condensing 3-(3R)-(toluene-4-sulfonyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester with (R)-(−)-2-methylpyrrolidine (obtained from Advanced Asymmetrics).

Sources & evidence

ORD record
ord-0cf4bc42c18245f7aff2d267f765950f
Source dataset
uspto-grants-2014_08
Patent number
US08796278B2

Reaction notes

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