tert-Butyl methyl((3R)-pyrrolidin-3-yl)carbamate → (3R)-(-)-1-Benzyl-3-(methylamino)pyrrolidine

HRID 2425402Notes

Reaction equation

HRID 2425402 reaction equation
C(OC(N([C@@H]1CCN(S([C:18]2[C:19]3[C:20](Br)=[CH:21][N:22]=[CH:23][C:24]=3[CH:25]=[CH:26][CH:27]=2)(=O)=O)C1)C)=O)(C)(C)C.C(O[C:34]([N:36]([C@@H:38]1CCN[CH2:39]1)C)=O)(C)(C)C>>[CH2:23]([N:22]1[CH2:21][CH2:20][C@@H:38]([NH:36][CH3:34])[CH2:39]1)[C:24]1[CH:19]=[CH:18][CH:27]=[CH:26][CH:25]=1

Participants

3

Reactant 2

HCID 7019173tert-Butyl methyl((3R)-pyrrolidin-3-yl)carbamateHCID 67243638HCID 67243638, compound2×

Product 1

HCID 10035441(3R)-(-)-1-Benzyl-3-(methylamino)pyrrolidine

Procedure

(R)-3-[N-(tert-Butoxycarbonyl)-N-methylamino]-1-(4-bromo-5-isoquinolinesulfonyl)pyrrolidine (Intermediate 20b) can be prepared by using (R)-3-[N-(tert-butoxycarbonyl)-N-methylamino]pyrrolidine obtained from (R)-1-benzyl-3-(methylamino)pyrrolidine (Tokyo Kasei Kogyo) instead of (S)-3-[N-(tert-butoxycarbonyl)-N-methylamino]pyrrolidine according to the method described in a known literature (Barlocco et al., Tetrahedron, 1995, 51, 11547) in Example 1-3, Step A, and used in the method of Example 1-3, Step B in a similar manner to obtain the title compound as hydrochloride.

Sources & evidence

ORD record
ord-4ab9924a22bf47368f7285158b83f882
Source dataset
uspto-grants-2011_06
Patent number
US07964613B2

Reaction notes

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