HCID 20694310, compound → HCID 20694280, compound

HRID 380534Notes

Reaction equation

[Cl:1][C:2]1[CH:45]=[C:44]([Cl:46])[CH:43]=[CH:42][C:3]=1[CH2:4][N:5]1[CH2:9][C@H:8]([C:10]2[CH:14]=[CH:13][S:12][CH:11]=2)[C@@H:7]([CH2:15][N:16]2[CH2:21][CH2:20][CH:19]([CH2:22][CH:23]([O:31]C(=O)[C@H](C3C=CC=CC=3)C)[CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:18][CH2:17]2)[CH2:6]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Cl:1][C:2]1[CH:45]=[C:44]([Cl:46])[CH:43]=[CH:42][C:3]=1[CH2:4][N:5]1[CH2:9][C@H:8]([C:10]2[CH:14]=[CH:13][S:12][CH:11]=2)[C@@H:7]([CH2:15][N:16]2[CH2:17][CH2:18][CH:19]([CH2:22][CH:23]([OH:31])[CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:20][CH2:21]2)[CH2:6]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 0.1107 g (0.16 mmol) of 1-(2,4-dichlorobenzyl)-3-(S)-(4-(3-phenyl-2-((S)-2-phenylpropionyl)oxypropyl)piperidinylmethyl)-4-(S)-(3-thienyl)pyrrolidine (isomer 1) in 2 ml of THF at 0° C. was added 0.5 mL (0.5 mmol) of a 1 M solution of LiAlH4 in THF. The solution was stirred at 0° C. for 1 h, then was quenched by addition of 0.5 mL of 5N NaOH solution. The mixture was diluted with ethyl acetate, dried over MgSO4, filtered and the filtrate concentrated. The residue was purified by chromatography (silica, hexanes:acetone, 4:1) to give the title compound. Mass Spectrum (ESI) m/e=543 (M+1 35Cl, 35Cl), 545 (M+1 35Cl, 37Cl), and 547 (M+1 37Cl, 37Cl). [α]D=+11.7 (c=1.54, CHCl3).

Workup

customwas quenched by addition of 0.5 mL of 5N NaOH solution
additionThe mixture was diluted with ethyl acetate
dry with materialdried over MgSO4
filtrationfiltered
concentrationthe filtrate concentrated
customThe residue was purified by chromatography (silica, hexanes:acetone, 4:1)

Sources & evidence

ORD record: ord-eb4112535cdc46f694114540e5738237
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06303593B1

Reaction notes

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