4-Toluenesulfonyl chloride → 1-Oxa-8-azaspiro[4.5]decane-8-carboxylic acid, 4-hydroxy-, 1,1-diMethylethyl ester

HRID 747015Notes

Reaction equation

HRID 747015 reaction equation
[OH:1][CH:2]([C:6]1([OH:19])[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)[CH2:3][CH2:4]O.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.C(N(CC)CC)C>ClCCl>[OH:1][CH:2]1[C:6]2([CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])[CH2:10][CH2:11]2)[O:19][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471Triethylamine2×HCID 69714411HCID 69714411, compound

Product 1

HCID 697044001-Oxa-8-azaspiro[4.5]decane-8-carboxylic acid, 4-hydroxy-, 1,1-diMethylethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-(1,3-dihydroxypropyl)-4-hydroxypiperidine-1-carboxylate (from step (ii) above; 480 mg) was dissolved in dichloromethane and p-toluenesulfonyl chloride was added followed by triethylamine (0.49 mL) and the mixture was stirred for 12 h. An additional aliquot of triethylamine was added (0.49 mL) and the mixture stirred for 48 h. This mixture was concentrated in vacuo. The crude product was purified by chromatography on silica using 50-95% ethyl acetate in iso-hexane as eluant to afford the product (300 mg).

Workup

  1. stirringthe mixture stirred for 48 h
  2. concentrationThis mixture was concentrated in vacuo
  3. customThe crude product was purified by chromatography on silica using 50-95% ethyl acetate in iso-hexane as eluant

Sources & evidence

ORD record
ord-42c5010fd39d4ee588c0df4a895f71bb
Source dataset
uspto-grants-2008_07
Patent number
US07393858B2

Reaction notes

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