Sodium Hydroxide → HCID 86754942, compound

HRID 611604Notes

Reaction equation

HRID 611604 reaction equation
[OH-].[Na+].[CH3:3][C@@H:4]([N:11]1[CH2:15][CH2:14][C@@H:13]([CH2:16][OH:17])[CH2:12]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.Br[CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C1(C)C=CC=CC=1>[C:5]1([C@H:4]([N:11]2[CH2:15][CH2:14][C@@H:13]([CH2:16][O:17][CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:12]2)[CH3:3])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 79177tert-Butyl bromoacetateHCID 13772858{(3R)-1-[(1R)-1-Phenylethyl]pyrrolidin-3-yl}methanol

Product 1

HCID 86754942HCID 86754942, compound

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolvent2×

Procedure

20 mg of tetrabutylammonium bromide in 1 ml of water and then within 5 min. 20 g of 50% NaOH in water are added dropwise to a mixture of 2.05 g of (R)-1-[(R)-α-methylbenzyl]-3-pyrrolidinemethanol, 25 ml of toluene and 2.2 ml of tert.-butyl bromoacetate while stirring vigorously. After 6.5 hrs. the mixture is diluted with toluene, washed neutral with water, dried and evaporated in a vacuum. Chromatography on silica gel gives 2.1 g of tert.-butyl (R)-[1-(R)-[1-phenyl-ethyl]-pyrrolidin-3-ylmethoxy]-acetate, [α]D =+29.2°, (MeOH, c=1.0), MS: 319 (M)+.

Workup

  1. washwashed neutral with water
  2. customdried
  3. customevaporated in a vacuum

Sources & evidence

ORD record
ord-680f5c298c9744d1979755636f2a28b6
Source dataset
uspto-grants-1999_12
Patent number
US06001855

Reaction notes

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