Ethyl Acetate → Benzyl [3-chloro-4-(1,4-dioxaspiro[4.5]dec-8-yl)phenyl]carbamate

HRID 1713889Notes

Reaction equation

HRID 1713889 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[C:9]1[CH2:18][CH2:17][C:12]2([O:16][CH2:15][CH2:14][O:13]2)[CH2:11][CH:10]=1)[NH2:5].[C:19]([O:22][CH2:23][CH3:24])(=[O:21])C>[Pt]=O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][C:19](=[O:21])[O:22][CH2:23][C:24]2[CH:4]=[CH:3][CH:2]=[CH:8][CH:7]=2)[CH:6]=[CH:7][C:8]=1[CH:9]1[CH2:18][CH2:17][C:12]2([O:13][CH2:14][CH2:15][O:16]2)[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 594640703-Chloro-4-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)benzenamine

Product 1

HCID 59464044Benzyl [3-chloro-4-(1,4-dioxaspiro[4.5]dec-8-yl)phenyl]carbamate

Reagents, catalysts & solvents 1

HCID 82844Platinum oxide (PtO)Catalyst2×

Procedure

Platinum oxide (250 mg) was added in one portion to a stirred solution of 3-chloro-4-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)aniline (3.4 g, 12.8 mmol) in ethyl acetate (50 mL) and the mixture was stirred at room temperature under a hydrogen atmosphere for 9 h. A further portion of platinum oxide (250 mg) was added in one portion and the mixture was stirred for 8 h at room temperature under a hydrogen atmosphere. The reaction mixture was filtered and concentrated in vacuo to leave the cyclohexane-aniline product (2.1 g) as a solid, which was used with no further purification.

Workup

  1. stirringthe mixture was stirred for 8 h at room temperature under a hydrogen atmosphere
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b4f3c93c69964ad1a290d8ec4c6912a8
Source dataset
uspto-grants-2010_09
Patent number
US07795283B2

Reaction notes

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