[C:1]1([CH2:7][N:8]2[CH2:12][C@H:11]([C:13](OC)=[O:14])[C@H:10]([C:17](OC)=[O:18])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].CCOCC.[OH-].[Na+]>C1COCC1.O>[C:1]1([CH2:7][N:8]2[CH2:12][C@H:11]([CH2:13][OH:14])[C@H:10]([CH2:17][OH:18])[CH2:9]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1Dimethyl (cis)-1-(phenylmethyl)-3,4-pyrrolidinedicarboxylate (Chem. Pharm. Bull. 1985 33; 896-898) (2.44 g, 8.8 mmol) was dissolved in THF (100 mL) and cooled to 0° C. LiAlH4 (1 g, 26 mmol) was added in portions and the reaction was heated overnight at 60° C. Upon cooling to 0° C., wet ether was added followed by water (1 mL), 15 w/w NaOH (aq) (1 mL) and water (3 mL). The resulting mixture was stirred for 15 min and filtered through Celite yielding crude [(cis)-1-(phenylmethyl)-3,4-pyrrolidinediyl]dimethanol (2.5 g) which was used directly in the next reaction. LCMS: (M+H)+: 222.3.
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