HCID 58137332, compound → HCID 58137324, compound

HRID 1424574Notes

Reaction equation

HRID 1424574 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[CH:23]([CH3:29])[C:24]([O:26][CH2:27][CH3:28])=[O:25]>C(O)(C(F)(F)F)=O>[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[CH:23]([CH3:29])[C:24]([O:26][CH2:27][CH3:28])=[O:25]

Participants

3

Reactant 1

HCID 58137332HCID 58137332, compound

Product 1

HCID 58137324HCID 58137324, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Tert-butyl 7-bromo-3-(1-ethoxy-1-oxopropan-2-yl)-2,3-dihydrospiro[indene-1,4′-piperidine]-1′-carboxylate (300 mg, 0.645 mol) was dissolved in 20% TFA at 0° C. The reaction mixture was stirred for 1′ h at rt. The solvent was removed under reduced pressure to give ethyl 2-(7-bromo-2,3-dihydrospiro[indene-1,4′-piperidine]-3-yl)propanoate (235 mg, 100%). 1H NMR: (400 MHz, CDCl3): δ=0.98 (d, 3H), 1.23 (t, 3H), 1.61-1.73 (m, 4H), 2.42 (m, 1H), 2.73 (m, 1H), 3.01 (m, 1H), 3.23 (m, 3H), 3.48 (m, 3H), 3.68 (d, 1H), 4.21 (q, 2H), 7.03 (m, 2H), 7.38 (d, 1H).

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-6fcfdfd3af8d47a180f5c1448505366c
Source dataset
uspto-grants-2015_01
Patent number
US08927715B2

Reaction notes

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