Methyl chloroformate → (+/-)-methyl (4-chloro-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methylcarbamate

HRID 13951Notes

Reaction equation

HRID 13951 reaction equation
[Cl:1][C:2]1[C:13]2[CH2:12][CH:11]([CH2:14][NH2:15])[O:10][C:9]=2[C:8]2[CH2:7][CH2:6][CH2:5][C:4]=2[CH:3]=1.C(N(C(C)C)CC)(C)C.Cl[C:26]([O:28][CH3:29])=[O:27].CC1C=CC(S(OC)(=O)=O)=CC=1>>[Cl:1][C:2]1[C:13]2[CH2:12][CH:11]([CH2:14][NH:15][C:26](=[O:27])[O:28][CH3:29])[O:10][C:9]=2[C:8]2[CH2:7][CH2:6][CH2:5][C:4]=2[CH:3]=1

Participants

5

Reactant 4

HCID 6586Methyl chloroformateHCID 6645Methyl p-toluenesulfonateHCID 81531DiisopropylethylamineHCID 11413423(+/-)-1-(4-chloro-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methanamine

Product 1

HCID 86598562(+/-)-methyl (4-chloro-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methylcarbamateYield 92.6%

Procedure

Treatment of (±)-1-(4-chloro-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methanamine hydrochloric salt (0.60 g, 2.3 mmol) with diisopropylethylamine (0.89 g, 6.9 mmol) and methyl chloroformate (0.44 g, 4.6 mmol) generally according to the procedure described for Intermediate 7 provided 0.6 g of (±)-methyl (4-chloro-3,6,7,8-tetrahydro-2H-indeno[4,5-b]furan-2-yl)methylcarbamate as white solid. mp 139-141° C.; Anal. calcd. for C14H16ClNO3: C, 59.68; H, 5.72; N, 4.97. Found: C, 58.99; H, 5.72; N, 4.86.

Sources & evidence

ORD record
ord-fbd596be660e402eb2f25d524b5ff3cf
Source dataset
uspto-grants-2010_06
Patent number
US07728155B2

Reaction notes

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