Water → HCID 131716299, compound

HRID 345328Notes

Reaction equation

HRID 345328 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([CH2:13][C:14](O)=[O:15])[CH2:10][C@@H:9]1[C:17]([O:19][CH3:20])=[O:18])=[O:7])([CH3:4])([CH3:3])[CH3:2].B.O>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([CH2:13][CH2:14][OH:15])[CH2:10][C@@H:9]1[C:17]([O:19][CH3:20])=[O:18])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 6331BoraneHCID 131716300HCID 131716300, compound

Product 1

HCID 131716299HCID 131716299, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 0.67 g of cis methyl N-t-butoxycarbonyl-4-(carboxymethyl)-pyrrolidine-2-carboxylate in 1 ml THF is added at 0° 3.5 ml of borane (1M) in THF. After stirring 0.5 hour, 1 ml of water is added, the solvent is evaporated and the residue is flash chromatographed with ethyl acetate/hexane (75:25) to afford cis methyl N-t-butoxycarbonyl-4-(2-hydroxyethyl)-pyrrolidine-2-carboxylate.

Workup

  1. customthe solvent is evaporated
  2. customchromatographed with ethyl acetate/hexane (75:25)

Sources & evidence

ORD record
ord-c808508c4e534c50acdb6170ee8d7b53
Source dataset
uspto-grants-1991_10
Patent number
US05057506

Reaction notes

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