Potassium bis(trimethylsilyl)amide → HCID 18723515, compound

HRID 842236Notes

Reaction equation

[CH3:1][Si]([N-][Si](C)(C)C)(C)C.[K+].[C:11]1([C:21]([N:23]2[CH2:27][CH:26]([CH:28]=O)[CH:25]([CH2:30][N:31]3[CH2:36][CH2:35][CH:34]([C:37]4[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=4)[CH2:33][CH2:32]3)[CH2:24]2)=[O:22])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[C:11]1([C:21]([N:23]2[CH2:27][CH:26]([CH:28]=[CH2:1])[CH:25]([CH2:30][N:31]3[CH2:32][CH2:33][CH:34]([C:37]4[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=4)[CH2:35][CH2:36]3)[CH2:24]2)=[O:22])[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of 0.08 g (0.22 mmol) of methyltriphenyl phosphonium bromide (Ph3PCH3Br) in 4 mL of THF at rt was added 0.36 mL of potassium bis(trimethylsilyl)amide and the reaction mixture was stirred for 30 min. The reaction mixture was cooled to 0° C. and to it was added a solution of 0.04 g (0.089 mmol) of 1-(1-naphthoyl)-3-(RS)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(SR)-formylpyrrolidine in 2 mL of THF. The reaction mixture was warmed to rt and stirred for 1.2 h. The reaction mixture was filtered through a thin pad of silica eluting with acetone:hexanes, 1:2, then concentrated. The residue was purified by chromatography (silica, acetone:hexanes, 1:2) to give the title compound. Mass Spectrum (ESI) m/e=444 (M+1).

Workup

temperatureThe reaction mixture was warmed to rt
stirringstirred for 1.2 h
filtrationThe reaction mixture was filtered through a thin pad of silica eluting with acetone
concentrationhexanes, 1:2, then concentrated
customThe residue was purified by chromatography (silica, acetone:hexanes, 1:2)

Sources & evidence

ORD record: ord-6990f1ea46a4402990ae05c3ea28d6b5
Source dataset: uspto-grants-2002_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06372764B1

Reaction notes

Loading…