Methyl 1-benzyl-4-phenylpyrrolidine-3-carboxylate → 1-Benzyl-4-phenyl-3-pyrrolidinemethanol

HRID 1276485Notes

Reaction equation

[C:1]1([CH2:7][N:8]2[CH2:12][CH:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:10]([C:19](OC)=[O:20])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].C([Al+]CC(C)C)C(C)C>C1COCC1.C1(C)C=CC=CC=1>[C:1]1([CH2:7][N:8]2[CH2:12][CH:11]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:10]([CH2:19][OH:20])[CH2:9]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 2.61 g (8.8 mmol) of 1-phenylmethyl-3-(SR)-carbomethoxy-4-(SR)-phenylpyrrolidine (from Example 1, Step A) in 100 mL of THF at -78 ° C. was treated with 9.2 mL of 1.5 M diisobutyl-aluminum hydride solution in toluene. The reaction was warmed to 0 ° C. and stirred for 1 h. The reaction was quenched with 50 mL of sat'd sodium potassium tartrate solution, diluted with 100 mL of ether and stirred at rt for 20 h. The layers were separated and the organic layer was washed with 75 mL of H2O, dried over MgSO4 and concentrated in vacuo. Flash chromatography on 100 g of silica gel using 1:1 v/v, then 3:2 v/v EtOAc/hexanes as the eluant afforded 1.99 g (84%) of the title compound as a solid. 1H NMR (500 MHz, CDCl3): δ2.56-2.63 (m, 1H), 2.80 (dd, J=4.3, 9.4, 1H), 2.91-2.98 (m, 2H), 3.05 (dd, J=6.9, 9.6, 1H), 3.27 (dd, J=5.0, 10.7, 1H), 3.44 (dd, J=5.5, 10.8, 1H), 3.62 (q, J=9.0, 1H), 3.76 (ABq, J=24.2, 2H), 7.22-7.40 (10H). Mass Spectrum (NH3 -CI): m/z 268 (M+1).

Workup

customThe reaction was quenched with 50 mL of sat'd sodium potassium tartrate solution
additiondiluted with 100 mL of ether
stirringstirred at rt for 20 h
customThe layers were separated
washthe organic layer was washed with 75 mL of H2O
dry with materialdried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-13606ee539b84a40b272c67831573ec2
Source dataset: uspto-grants-2000_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06166037

Reaction notes

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