Benzyl Bromide → Ammonia

HRID 2387655Notes

Reaction equation

HRID 2387655 reaction equation
[C:1]([N:8]1[CH2:12][CH2:11][C@@H:10]([OH:13])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:14](Br)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[NH3:8].[CH2:14]([O:13][C@@H:10]1[CH2:11][CH2:12][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 7498Benzyl BromideHCID 6544479tert-Butyl (3R)-3-hydroxypyrrolidine-1-carboxylate

Product 2

HCID 222AmmoniaHCID 10826398HCID 10826398, compound

Procedure

The title compound was prepared from (R)-(−)-N-boc-3-pyrrolidinol and benzyl bromide, using the same method as that described for preparation 5. The crude compound was purified by column chromatography on silica gel, eluting with dichloromethane:methanol:0.88 ammonia, 95:5:0.5, to afford the desired product in 97% yield.

Workup

  1. customthat described for preparation 5
  2. customThe crude compound was purified by column chromatography on silica gel
  3. washeluting with dichloromethane

Sources & evidence

ORD record
ord-de0b5c75f2c945d6b37ddd329ed5ebe9
Source dataset
uspto-grants-2012_09
Patent number
US08268881B2

Reaction notes

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