Triethylamine → (8-Benzyl-9,9-dimethyl-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl)-(4-isopropoxy-3-methyl-phenyl)methanone

HRID 73052Notes

Reaction equation

HRID 73052 reaction equation
[CH:1]([O:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][C:6]=1[CH3:14])([CH3:3])[CH3:2].C(N(CC)CC)C.Cl.[CH2:23]([N:30]1[C:40]([CH3:42])([CH3:41])[CH2:39][O:38][C:32]2([CH2:37][CH2:36][NH:35][CH2:34][CH2:33]2)[CH2:31]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C(#N)C>[CH2:23]([N:30]1[C:40]([CH3:42])([CH3:41])[CH2:39][O:38][C:32]2([CH2:33][CH2:34][N:35]([C:9]([C:8]3[CH:12]=[CH:13][C:5]([O:4][CH:1]([CH3:2])[CH3:3])=[C:6]([CH3:14])[CH:7]=3)=[O:11])[CH2:36][CH2:37]2)[CH2:31]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 592729354-Isopropoxy-3-methylbenzoic acidHCID 708725958-Benzyl-9,9-dimethyl-11-oxa-3,8-diazaspiro[5.5]undecane hydrochloride

Product 1

HCID 70872805(8-Benzyl-9,9-dimethyl-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl)-(4-isopropoxy-3-methyl-phenyl)methanoneYield 70.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 4-isopropoxy-3-methylbenzoic acid (31.0 mg, 0.161 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N,N′-tetramethyluronium hexafluorophosphate (61.3 mg, 0.161 mmol) in acetonitrile was treated with triethylamine (67 μL, 0.48 mmol) and stirred for 5 min. 8-Benzyl-9,9-dimethyl-11-oxa-3,8-diazaspiro[5.5]undecane hydrochloride (56.0 mg, 0.161 mmol) was added and the reaction mixture stirred for 3 h. The reaction mixture was filtered and concentrated in vacuo. The crude material was purified by chromatography (0-80% of ethyl acetate/hexanes) to provide (8-benzyl-9,9-dimethyl-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl)-(4-isopropoxy-3-methyl-phenyl)methanone (51.0 mg, 70%) as colorless oil. ESI-MS m/z calc. 450.6. Found 451.3 (M+1)+; Retention time: 1.54 minutes (3 min run).

Workup

  1. stirringthe reaction mixture stirred for 3 h
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated in vacuo
  4. customThe crude material was purified by chromatography (0-80% of ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-9739485eb47b4b29a88018f97e8a51ea
Source dataset
uspto-grants-2014_09
Patent number
US08828996B2

Reaction notes

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