Water → ((S)-1-((S)-1-phenylethyl)pyrrolidin-3-yl)methanol

HRID 383864Notes

Reaction equation

HRID 383864 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].O=[C:8]1[N:12]([C@H:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH3:14])[CH2:11][C@@H:10]([C:21](OC)=[O:22])[CH2:9]1.O.[OH-].[Na+]>C1COCC1>[C:15]1([C@@H:13]([N:12]2[CH2:8][CH2:9][C@H:10]([CH2:21][OH:22])[CH2:11]2)[CH3:14])[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 13772856HCID 13772856, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 11084986((S)-1-((S)-1-phenylethyl)pyrrolidin-3-yl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of LAH (20 g, 0.526 mol) in dried THF (400 mL) was added dropwise a solution of (S)-methyl 5-oxo-1-((S)-1-phenylethyl)pyrrolidine-3-carboxylate (50 g, 0.202 mol) in dried THF (50 mL) at 0° C. The mixture was heated to reflux overnight. The reaction mixture was cooled to 0° C. and treated with water (20 mL) and aqueous NaOH (10%, 20 mL). The slurry formed was filtered off and washed with THF. The combined filtrate was evaporated to give compound ((S)-1-((S)-1-phenylethyl)pyrrolidin-3-yl)methanol, which was used directly in the next step.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. customThe slurry formed
  4. filtrationwas filtered off
  5. washwashed with THF
  6. customThe combined filtrate was evaporated

Sources & evidence

ORD record
ord-74bd000b979c4aee949ea5905655251d
Source dataset
uspto-grants-2013_02
Patent number
US08367691B2

Reaction notes

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