Water → [(3R,4S)-1-Benzyl-4-(4-chloro-phenyl)-pyrrolidin-3-yl]-methanol

HRID 1880224Notes

Reaction equation

HRID 1880224 reaction equation
C[O:2][C:3]([C@@H:5]1[C@@H:9]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[CH2:8][N:7]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:6]1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[CH2:17]([N:7]1[CH2:8][C@H:9]([C:10]2[CH:11]=[CH:12][C:13]([Cl:16])=[CH:14][CH:15]=2)[C@@H:5]([CH2:3][OH:2])[CH2:6]1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 53485150Trans-methyl 1-benzyl-4-(4-chlorophenyl)pyrrolidine-3-carboxylate

Product 1

HCID 67532159[(3R,4S)-1-Benzyl-4-(4-chloro-phenyl)-pyrrolidin-3-yl]-methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(3R,4S)-1-Benzyl-4-(4-chloro-phenyl)-pyrrolidine-3-carboxylic acid methyl ester (5.8 g, 0.018 mol) were dissolved in THF (180 mL). At 0° C. LiAlH4 (0.70 g, 0.0185 mol) was added portion wise. After stirring at 0° C. for 4 h water (5 mL), then 5N NaOH (5 mL) and additional water (15 mL) was added. After stirring at ambient temperature for 30 min the mixture was extracted with ethyl acetate (3×10 mL), the combined organic phases were dried on sodium sulfate, filtered and evaporated. The crude title product was obtained as a light yellow oil (5.2 g, 98%) and directly used in the next step. ES-MS m/e: 302.8 (M+H+).

Workup

  1. customAt 0° C
  2. extractionwas extracted with ethyl acetate (3×10 mL)
  3. customthe combined organic phases were dried on sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-c554abff737f4d03b6df70024a2485ca
Source dataset
uspto-grants-2012_11
Patent number
US08318759B2

Reaction notes

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