Triethylamine → Benzyl-carbamic acid 1-[2,3-dimethoxy-6-(1-oxo-indan-4-yl)-phenoxymethyl]-cyclopropylmethyl ester

HRID 2171022Notes

Reaction equation

HRID 2171022 reaction equation
[OH:1][CH2:2][C:3]1([CH2:6][O:7][C:8]2[C:13]([O:14][CH3:15])=[C:12]([O:16][CH3:17])[CH:11]=[CH:10][C:9]=2[C:18]2[CH:26]=[CH:25][CH:24]=[C:23]3[C:19]=2[CH2:20][CH2:21][C:22]3=[O:27])[CH2:5][CH2:4]1.C(N(CC)CC)C.[CH2:35]([N:42]=[C:43]=[O:44])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.COC1C(OC)=CC=C(C2C=CC=C3C=2CCC3=O)C=1OCC1(COC(=O)NCC)CC1>ClCCl>[CH3:15][O:14][C:13]1[C:12]([O:16][CH3:17])=[CH:11][CH:10]=[C:9]([C:18]2[CH:26]=[CH:25][CH:24]=[C:23]3[C:19]=2[CH2:20][CH2:21][C:22]3=[O:27])[C:8]=1[O:7][CH2:6][C:3]1([CH2:2][O:1][C:43](=[O:44])[NH:42][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 76639Benzyl isocyanateHCID 545762924-[2-(1-Hydroxymethyl-cyclopropylmethoxy)-3,4-dimethoxy-phenyl]-indan-1-one2×HCID 71279321Ethyl-carbamic acid 1-[2,3-dimethoxy-6-(1-oxo-indan-4-yl)-phenoxymethyl]-cyclopropylmethyl ester

Product 1

HCID 54577166Benzyl-carbamic acid 1-[2,3-dimethoxy-6-(1-oxo-indan-4-yl)-phenoxymethyl]-cyclopropylmethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 4-[2-(1-Hydroxymethyl-cyclopropylmethoxy)-3,4-dimethoxy-phenyl]-indan-1-one (Compound 177) (150 mg, 0.407 mmol) in dichloromethane (15 mL), were added triethylamine (123 mg, 1.222 mmol) and benzyl isocyanate (105 mg, 0.812 mmol) and the resultant reaction mixture was subjected to the conditions used in the preparation of Compound 179 to afforded the title compound as a solid.

Workup

  1. customthe resultant reaction mixture

Sources & evidence

ORD record
ord-40b732b6ad1d465a90b9442c2591e311
Source dataset
uspto-grants-2015_06
Patent number
US09051290B2

Reaction notes

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