Lithium borohydride → 1,1-Dimethylethyl (2R,4R)-2-(hydroxymethyl)-4-(phenylmethoxy)-1-pyrrolidinecarboxylate

HRID 732376Notes

Reaction equation

HRID 732376 reaction equation
[BH4-].[Li+].C[O:4][C:5]([C@H:7]1[CH2:11][C@@H:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][N:8]1[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=O>O1CCCC1>[C:23]([O:22][C:20]([N:8]1[CH2:9][C@H:10]([O:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:11][C@@H:7]1[CH2:5][OH:4])=[O:21])([CH3:26])([CH3:25])[CH3:24]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 68814950HCID 68814950, compound

Product 1

HCID 688152181,1-Dimethylethyl (2R,4R)-2-(hydroxymethyl)-4-(phenylmethoxy)-1-pyrrolidinecarboxylateYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add lithium borohydride (0.0097 g, 0.44 mmol) to an ice cold solution of (2R,4R)-4-benzyloxypyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (0.1 g, 0.29 mmol) in tetrahydrofuran (1 mL). Warm slowly to room temperature over 18 hours. Cool in ice bath. Slowly add acetone (1 mL), concentrate and purify (silica gel chromatography, eluting with ethyl acetate/hexanes mixtures) to give the title compound as a colorless oil (0.071 g, 80%).

Workup

  1. temperatureCool in ice bath
  2. concentrationSlowly add acetone (1 mL), concentrate
  3. custompurify
  4. wash(silica gel chromatography, eluting with ethyl acetate/hexanes mixtures)

Sources & evidence

ORD record
ord-ebe50828622c4ca88b1265eb07a8d5ed
Source dataset
uspto-grants-2009_09
Patent number
US07585885B2

Reaction notes

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