Dichloromethane → Tert-butyl 4-(2-hydroxyphenyl)piperidine-1-carboxylate

HRID 2377800Notes

Reaction equation

HRID 2377800 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[OH:13])[CH2:3][CH2:2]1.C([O-])(O)=O.[Na+].[O:19](C(OC(C)(C)C)=O)[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=O.C(Cl)Cl>O.C1COCC1>[C:23]([O:22][C:20]([N:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[OH:13])[CH2:3][CH2:2]1)=[O:19])([CH3:26])([CH3:25])[CH3:24]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 90495Di-tert-butyl dicarbonateHCID 516892Sodium BicarbonateHCID 107024522-(Piperidin-4-yl)phenol

Product 1

HCID 17174861Tert-butyl 4-(2-hydroxyphenyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of the hydrobromide salt of 2-piperidin-4-yl-phenol Compound 3a (5.00 g, 19.37 mmol) in water (400 mL) was made basic to pH 8 by the addition of NaHCO3. A solution of O(Boc)2 (4.22 g, 19.36 mmol) in THF (80 mL) was added and the mixture was stirred at r.t. over night. CH2Cl2 (500 mL) was added and the organic layer was isolated and dried. The crude product was purified by chromatography to provide 4-(2-hydroxy-phenyl)-piperidine-1-carboxylic acid tert-butyl ester Compound 2a (4.56 g, 85%) as a white powder 1H NMR δ 1.50 (s, 9H), 1.60 (m, 2H), 1.85 (bd, J=19.5 Hz, 2H), 2.82 (bm, 2H), 3.04 (m, 1H), 4.23 (bs, 2H), 6.7˜7.2 (m, 4H).

Workup

  1. customthe organic layer was isolated
  2. customdried
  3. customThe crude product was purified by chromatography

Sources & evidence

ORD record
ord-eafd355a7661455f9dc6229b6634094b
Source dataset
uspto-grants-2008_12
Patent number
US07470711B2

Reaction notes

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