Pyrrolidine → HCID 11831606, compound

HRID 346461Notes

Reaction equation

HRID 346461 reaction equation
[C:1]([NH:8][C@H:9]([C:11]([OH:13])=O)[CH3:10])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[NH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1>>[C:1]([NH:8][C@H:9]([C:11]([N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:13])[CH3:10])([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 85082Tert-butoxycarbonylalanine

Product 1

HCID 11831606HCID 11831606, compound

Procedure

10.0 g (53 mmol) BOC-alanine was coupled to 8.7 ml (105 mmol) pyrrolidine according to procedure B. Yield of active ester 14.97 g (52 mmol, 98%). Yield of crude product 10.97 g. The product was purified by a silica column using 50–100% ethyl acetate in petroleum ether as eluent. Yield 9.07 g (37.4 mmol, 72%).

Workup

  1. customThe product was purified by a silica column

Sources & evidence

ORD record
ord-7528c2ebdff241f3bcb66b743a392c8f
Source dataset
uspto-grants-2007_02
Patent number
US07173024B2

Reaction notes

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