Triethylamine → Benzyl 3-oxo-2,3-dihydrospiro[indene-1,4'-piperidine]-1'-carboxylate

HRID 1695909Notes

Reaction equation

HRID 1695909 reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][C:5]2([C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9](=[O:16])[CH2:8]2)[CH2:4][CH2:3]1.CCN(CC)CC.[CH:24]1[CH:29]=[CH:28][C:27]([CH2:30][O:31][C:32](Cl)=[O:33])=[CH:26][CH:25]=1>C(Cl)Cl>[O:16]=[C:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:5]2([CH2:6][CH2:7][N:2]([C:32]([O:31][CH2:30][C:27]3[CH:28]=[CH:29][CH:24]=[CH:25][CH:26]=3)=[O:33])[CH2:3][CH2:4]2)[CH2:8]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 18673582Spiro[indene-1,4'-piperidin]-3(2H)-one--hydrogen chloride (1/1)

Product 1

HCID 59433376Benzyl 3-oxo-2,3-dihydrospiro[indene-1,4'-piperidine]-1'-carboxylateYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution spiro[indene-1,4′-piperidin]-3(2H)-one hydrochloride (5.0 g, 24.84 mmol) and Et3N (7.54 g, 74.53 mol) in CH2Cl2 (50 mL) was added drop-wise Cbz-Cl (4.66 g, 27.33 mmol) at 0° C. The reaction was allowed to warm to room temperature and stirred overnight. The precipitate was filtered, washed with Et2O and dried to furnish benzyl 3-oxo-2,3-dihydrospiro[indene-1,4′-piperidine]-1′-carboxylate (6.1 g, yield 99%).

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with Et2O
  3. customdried

Sources & evidence

ORD record
ord-2840ae1457bc4dab946ff52219988d1d
Source dataset
uspto-grants-2012_04
Patent number
US08163737B2

Reaction notes

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