Water → HCID 54185742, compound

HRID 1459699Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([OH:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:16][O:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Cl)=[CH:20][CH:19]=1.O>CN(C=O)C.CCOCC>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([O:13][CH2:22][C:21]2[CH:24]=[CH:25][C:18]([O:17][CH3:16])=[CH:19][CH:20]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of (3R)-N-tert-butyloxycarbonylpyrrolidin-3-ol (2.00 g, 10.7 mmol) in anhydrous DMF (12 ml) was added dropwise to a stirred slurry of sodium hydride (60% dispersion in oil, 0.465 g, 11.6 mmol) in DMF (25 ml) at -10° C. under nitrogen and the mixture stirred at this temperature for 0.67 h. 4-Methoxybenzyl chloride (1.52 ml, 11.2 mmol) was added dropwise and the mixture warmed to 0° C. over 1 h and then stirred at RT for 2 h. Water was added and the mixture poured into ether and washed with water (×3). The ethereal layer was dried (MgSO4), evaporated in uacuo and the crude product chromatographed on silica gel, eluting with ethyl acetate/hexane (30:70), to afford the title pyrrolidine (3.09 g, 94%),δ (250 MHz, CDCl3) 1.46 (9H, br s, OC(Me)3), 1.73-2.09 (2H, m, CH2), 3.40-3.46 (4H, m, 2 of CH2), 3.81 (3H, s, OMe), 4.12 (1H, m, CHOCH2Ar), 4.45 (2H, s, OCH2Ar), 6.85-6.91 (2H, m, Ar--H), 7.23-7.27 (2H, m, Ar--H).

Workup

stirringstirred at RT for 2 h
washwashed with water (×3)
dry with materialThe ethereal layer was dried (MgSO4)
customevaporated in uacuo
customthe crude product chromatographed on silica gel
washeluting with ethyl acetate/hexane (30:70)

Sources & evidence

ORD record: ord-fad892380d0c46c3903981c45a59ce48
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05854268

Reaction notes

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