2-adamantyl Chloroformate → (+/-)-(2-Adamantyl) 7-bromo-3-(2-ethoxy-2-oxoethyl)-2,3-dihydrospiro[indene-1,4'-piperidine]-1'-carboxylate

HRID 1424611Notes

Reaction equation

HRID 1424611 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:15]=1[C:9]1([CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)[CH2:8][CH:7]2[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].Cl[C:23]([O:25][CH:26]1[CH:33]2[CH2:34][CH:29]3[CH2:30][CH:31]([CH2:35][CH:27]1[CH2:28]3)[CH2:32]2)=[O:24]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:15]=1[C:9]1([CH2:10][CH2:11][N:12]([C:23]([O:25][CH:26]3[CH:27]4[CH2:35][CH:31]5[CH2:30][CH:29]([CH2:34][CH:33]3[CH2:32]5)[CH2:28]4)=[O:24])[CH2:13][CH2:14]1)[CH2:8][CH:7]2[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18]

Participants

4

Reactant 2

HCID 108785372-adamantyl ChloroformateHCID 58137336Ethyl 2-(7-bromo-2,3-dihydrospiro[indene-1,4'-piperidine]-3-yl)acetate

Product 1

HCID 66954223(+/-)-(2-Adamantyl) 7-bromo-3-(2-ethoxy-2-oxoethyl)-2,3-dihydrospiro[indene-1,4'-piperidine]-1'-carboxylateYield 39.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 100-mL flask was charged with (±)-ethyl 2-(7-bromo-2,3-dihydrospiro[indene-1,4′-piperidine]-3-yl)acetate (457 mg, 1.3 mmol) dissolved in dry CH2Cl2 (10 mL). TEA (394 mg, 3.9 mmol) was added at 0° C. and stirred for 1 h. 2-adamantyl chloroformate (301 mg, 1.4 mmol) was added and the mixture was stirred overnight. The mixture was concentrated to give a residue was purified by column chromatography to give (±)-(2-adamantyl) 7-bromo-3-(2-ethoxy-2-oxoethyl)-2,3-dihydrospiro[indene-1,4′-piperidine]-1′-carboxylate (270 mg, 39%). The enantiomers were separated by chiral HPLC to give isomer 1 (100 mg, 14%) and isomer 2 (100 mg, 14%).

Workup

  1. stirringthe mixture was stirred overnight
  2. concentrationThe mixture was concentrated
  3. customto give a residue
  4. customwas purified by column chromatography

Sources & evidence

ORD record
ord-43749e0790ab43cc9d6074e1d7f799ec
Source dataset
uspto-grants-2015_01
Patent number
US08927715B2

Reaction notes

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