Diethyl (2-amino-2-oxoethyl)phosphonate → E-N-Cyclopropyl-2-(7-fluoro-1,2,3,4-tetrahydro-1-naphthylidene)acetamide

HRID 862777Notes

Reaction equation

HRID 862777 reaction equation
C(CP(=O)(OCC)OCC)(=O)N.[F:13][C:14]1[CH:23]=[C:22]2[C:17]([CH2:18][CH2:19][CH2:20][C:21]2=O)=[CH:16][CH:15]=1.C(OP([CH2:33][C:34](=[O:39])[NH:35][CH:36]1[CH2:38][CH2:37]1)(=O)OCC)C>>[CH:36]1([NH:35][C:34](=[O:39])/[CH:33]=[C:21]2\[CH2:20][CH2:19][CH2:18][C:17]3[C:22]\2=[CH:23][C:14]([F:13])=[CH:15][CH:16]=3)[CH2:38][CH2:37]1

Participants

4

Reactant 3

HCID 225722Diethyl (2-amino-2-oxoethyl)phosphonateHCID 103747647-Fluoro-1,2,3,4-tetrahydronaphthalen-1-oneHCID 54270018Diethyl [2-(cyclopropylamino)-2-oxoethyl]phosphonate

Product 1

HCID 69886926E-N-Cyclopropyl-2-(7-fluoro-1,2,3,4-tetrahydro-1-naphthylidene)acetamideYield 37%

Procedure

This compound was prepared in an analogous manner to Example 27d with the replacement of 6-chloro-1-indanone and diethyl carbamoylmethylphosphonate with 7-fluoro-1-tetralone (7.76 g, 0.05 mol) and diethyl(cyclopropylcarbamoyl)methylphosphonate (11.1 g, 0.05 mol). Chromatography on Silica gel using ethyl acetate:hexanes (1:2) as eluent gave 4.38 g (37%) of (E)-N-Cyclopropyl-2-(7-fluoro-1,2,3,4-tetrahydro-1-naphthylidene)acetamide, m.p., 122.8°-123.3° C.; NMR (DMSO-d6): d 8.00 (d, J=4.0 Hz, 1H), 7.32 (dd, J=11.2 Hz, 1H), 7.04-7.23 (m, 2H), 6.33 (s, 1H), 3.06 (m,2H), 2.69 (m, 3H), 1.70 (m, 2H), 0.66 (m, 2H), 0.40 (m, 2H); steady-state nOe: irradiation at 6.39 d, observed significant nOe at 7.32 d.

Sources & evidence

ORD record
ord-2c869bab05bb416096af7d83a5e495dd
Source dataset
uspto-grants-1998_02
Patent number
US05719186

Reaction notes

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