Water → HCID 10025673, compound

HRID 1587645Notes

Reaction equation

[CH3:1][CH2:2][N:3]([CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12](/[C:15](/[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[C:16](/Cl)\[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[CH:13][CH:14]=1)[CH2:4][CH3:5].C([Li])(C)(C)C.[CH2:35]1[O:38][CH2:37][CH2:36]1.O>O1CCCC1>[CH3:1][CH2:2][N:3]([CH2:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12](/[C:15](/[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[C:16](\[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)/[CH2:35][CH2:36][CH2:37][OH:38])=[CH:13][CH:14]=1)[CH2:4][CH3:5]

Participants

Conditions

Temperature: -40 °C

Procedure

Clomiphene (3.8 g, 9.3 mmol) was dissolved in tetrahydrofuran (50 ml), cooled to -40° C. and then treated with t-butyl lithium (1M in pentane, 20 mmol). After 10 minutes, trimethylene oxide (6 ml, 93 mmol) was added, the mixture stirred for 16 hours at room temperature, and then poured into water. The product was extracted with ether and chromatographed on a silica gel column using 1:1:0.1 ether/petroleum ether/triethylamine as eluant to yield purified trans-product (1 g, 25%), m.p. 93°-95° C. and cis- product (N,N-diethylhydroxymethyl tamoxifen) (1.0 g, 25%), m.p. 85°-87° C. Anal. (C29H35NO2)C,H,N. Calc., C:81.08, H:8.21, N:3.26; Found, C:80.56, H:7.94, N:3.32. Values for aliphatic protons are presented in Table 3.

Workup

extractionThe product was extracted with ether
customchromatographed on a silica gel column
customto yield
custompurified trans-product (1 g, 25%), m.p. 93°-95° C. and cis- product (N,N-diethylhydroxymethyl tamoxifen) (1.0 g, 25%), m.p. 85°-87° C

Sources & evidence

ORD record: ord-94d12c54c81c493692abf14a9094db42
Source dataset: uspto-grants-1993_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05219548

Reaction notes

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