Monobenzone → Tert-butyl 4-[4-(benzyloxy)phenoxy]piperidine-1-carboxylate

HRID 2185476Notes

Reaction equation

HRID 2185476 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][CH:30]([OH:33])[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:22])[CH3:21].[CH2:34]([O:41][C:42]1[CH:47]=[CH:46][C:45](O)=[CH:44][CH:43]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[C:20]([O:24][C:25]([N:27]1[CH2:32][CH2:31][CH:30]([O:33][C:45]2[CH:46]=[CH:47][C:42]([O:41][CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[CH:43][CH:44]=2)[CH2:29][CH2:28]1)=[O:26])([CH3:23])([CH3:21])[CH3:22]

Participants

6

Reactant 4

HCID 7638MonobenzoneHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

Product 1

HCID 22458519Tert-butyl 4-[4-(benzyloxy)phenoxy]piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triphenylphosphine (917 mg) was added to a solution of N-tert-butoxycarbonyl-4-hydroxypiperidine (A, 704 mg), 4-benzyloxyphenol (700 mg) and diethyl azodicarboxylate (609 mg) in tetrahydrofuran (20 mL) at room temperature. After stirring at room temperature for 14 hr, the reaction mixture was concentrated in vacuo. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9, v/v) to give the titled compound (703 mg) as a colorless oil: 1H NMR (400 MHz, CDCl3) δ 1.47 (s, 9H), 1.72 (m, 2H), 1.88 (m, 2H), 3.29 (ddd, J=3.9, 7.8, 12.5 Hz, 2H), 3.70 (m, 2H), 4.32 (quintet, J=3.9 Hz, 1H), 5.01 (s, 2H), 6.84-6.91 (m, 4H), and 7.32-7.43 (m, 5H).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:9, v/v)

Sources & evidence

ORD record
ord-2b27f921ea6f46c59e1a174622be20bd
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

Loading…