1-Benzyl-3-(trifluoromethyl)pyrrolidine-3-carboxylic acid → (1-Benzyl-3-trifluoromethyl-pyrrolidin-3-YL)-methanol

HRID 1889Notes

Reaction equation

HRID 1889 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]([C:16]([F:19])([F:18])[F:17])([C:13](O)=[O:14])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:1]([N:8]1[CH2:12][CH2:11][C:10]([C:16]([F:18])([F:19])[F:17])([CH2:13][OH:14])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 196913671-Benzyl-3-(trifluoromethyl)pyrrolidine-3-carboxylic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 19691277(1-Benzyl-3-trifluoromethyl-pyrrolidin-3-YL)-methanolYield 99.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound from step 456a (2.32 g) was dissolved in 60 mL of dry THF, 1.12 eq of LAH (1N in dry THF) was added, and the reaction was stirred under N2 for 3 hours. The reaction was quenched by the sequential dropwise addition of 0.35 mL water, 0.35 mL of 15% NaOH and 1.3 mL of water, then the mixture was stirred for 1 hour and filtered. The filtrate was dried and concentrated to give 2.2 g of the title compound.

Workup

  1. customThe reaction was quenched by the sequential dropwise addition of 0.35 mL water, 0.35 mL of 15% NaOH and 1.3 mL of water
  2. stirringthe mixture was stirred for 1 hour
  3. filtrationfiltered
  4. customThe filtrate was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2fa90453573642919084e8719e36a12a
Source dataset
uspto-grants-1998_03
Patent number
US05726182

Reaction notes

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