Pyrrolidine → HCID 11088437, compound

HRID 346474Notes

Reaction equation

HRID 346474 reaction equation
[C:1]([NH:8][C@H:9]([C:17]([OH:19])=O)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[NH:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1>>[C:1]([NH:8][C@H:9]([C:17]([N:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1)=[O:19])[CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-

Product 1

HCID 11088437HCID 11088437, compound

Procedure

2.65 g (10 mmol) BOC-L phenylalanine was coupled to 1.48 ml (17.8 mmol) pyrrolidine according to procedure B. Yield of active ester 3.22 g (8.9 mmol, 89%). Yield of crude product 3.33 g. The product was purified with a silica column using 1–2% methanol in dichloromethane as eluent. Yield 1.76 g (5.5 mmol, 55%).

Workup

  1. customThe product was purified with a silica column

Sources & evidence

ORD record
ord-213fcc5d3d124d5a9115c7c650ac6d07
Source dataset
uspto-grants-2007_02
Patent number
US07173024B2

Reaction notes

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