Carbon tetrabromide → Ethyl 4-(3-bromopropyl)-1-(tert-butoxycarbonyl)piperidine-4-carboxylate

HRID 1777354Notes

Reaction equation

HRID 1777354 reaction equation
[C:1]([Br:5])(Br)(Br)Br.[CH2:6]([O:8][C:9]([C:11]1([CH2:24][CH2:25]CO)[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1)=[O:10])[CH3:7].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>ClCCl>[CH2:6]([O:8][C:9]([C:11]1([CH2:24][CH2:25][CH2:1][Br:5])[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]1)=[O:10])[CH3:7]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 578152391-Tert-butyl 4-ethyl 4-(3-hydroxypropyl)piperidine-1,4-dicarboxylate

Product 1

HCID 67539218Ethyl 4-(3-bromopropyl)-1-(tert-butoxycarbonyl)piperidine-4-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Carbon tetrabromide (1.6 gm, 0.0048 mol) is added to a stirred solution of 4-(3-hydroxypropyl) piperidine-1,4-dicarboxylic acid-1-tert-butyl ester-4-ethyl ester (1.27 gm, 0.0040 mol) and triphenyl phosphine (1.6 gm, 0.0060 mol) in dichloromethane (15 mL) at 0-5° C. temperature. Reaction mixture is allowed to stir at room temperature for 30 minutes. Removal of solvent gives a crude residue which is purified by column chromatography (silica gel 230-400 mesh, ethyl acetate:n-hexane 3:7) to get 4-(3-bromopropyl)piperidine-1,4-dicarboxylic acid-1-tert-butyl ester-4-ethyl ester.

Workup

  1. customReaction mixture
  2. customRemoval of solvent
  3. customgives a crude residue which
  4. customis purified by column chromatography (silica gel 230-400 mesh, ethyl acetate:n-hexane 3:7)

Sources & evidence

ORD record
ord-70e5d75e610f49728e35a6b0da7832f8
Source dataset
uspto-grants-2016_02
Patent number
US09266867B2

Reaction notes

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