Tert-butyl 7-bromo-3-(2-ethoxy-2-oxoethyl)-2,3-dihydrospiro[indene-1,4'-piperidine]-1'-carboxylate → Ethyl 2-(7-bromo-2,3-dihydrospiro[indene-1,4'-piperidine]-3-yl)acetate

HRID 1424610Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:22]=1[C:9]1([CH2:14][CH2:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]1)[CH2:8][CH:7]2[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25]>C(O)(C(F)(F)F)=O.C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:22]=1[C:9]1([CH2:10][CH2:11][NH:12][CH2:13][CH2:14]1)[CH2:8][CH:7]2[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25]

Participants

Conditions

Temperature: 0 °C

Procedure

A 100-mL of flask was charged with (±)-tert-butyl 7-bromo-3-(2-ethoxy-2-oxoethyl)-2,3-dihydrospiro[indene-1,4′-piperidine]-1′-carboxylate (500 mg, 1.1 mmol) dissolved in 20% TFA in CH2Cl2 solution (15 mL) at 0° C. The mixture was stirred for 0.5 h at 0° C. Then the mixture was concentrated to give crude (±)-ethyl 2-(7-bromo-2,3-dihydrospiro[indene-1,4′-piperidine]-3-yl)acetate which was used in the next step without further purification.

Workup

concentrationThen the mixture was concentrated

Sources & evidence

ORD record: ord-e04e4e72c86146dda622f4479e369bc7
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08927715B2

Reaction notes

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