Benzyl chloroformate → HCID 86601821, compound

HRID 2115921Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:14]([CH3:16])[CH3:15])[C:5]2[O:9][CH:8]([CH2:10][NH2:11])[CH2:7][C:6]=2[C:12]=1[CH3:13].C(N(C(C)C)CC)(C)C.Cl[C:27]([O:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:28]>>[CH2:30]([O:29][C:27](=[O:28])[NH:11][CH2:10][CH:8]1[CH2:7][C:6]2[C:12]([CH3:13])=[C:2]([Cl:1])[CH:3]=[C:4]([CH:14]([CH3:16])[CH3:15])[C:5]=2[O:9]1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

Reactant 3

HCID 10387Benzyl chloroformate

HCID 81531Diisopropylethylamine

HCID 68966057HCID 68966057, compound

Product 1

HCID 86601821HCID 86601821, compoundYield 81.3%

Procedure

Treatment of (±)-1-(5-chloro-7-isopropyl-4-methyl-2,3-dihydro-1-benzofuran-2-yl)methanamine (3.41 g, 12.3 mmol) with diisopropylethylamine (1.99 g, 14.2 mmol) and benzyl chloroformate (2.42 g, 14.2 mmol) generally according to the procedure described for Intermediate 12 gave 3.74 g (81%) of (±)-benzyl(5-chloro-7-isopropyl-4-methyl-2,3-dihydro-1-benzofuran-2-yl)methylcarbamate as a colorless oil. Anal. calcd. for C21H24ClNO3 C, 67.46; H, 6.47; N, 3.75. Found C, 67.01; H, 6.52; N, 3.56. Chiral HPLC separation of (±)-benzyl(5-chloro-7-isopropyl-4-methyl-2,3-dihydro-1-benzofuran-2-yl)methylcarbamate (Chiralpak AD, ethanol) provided two fractions.

Sources & evidence

ORD record: ord-1dee83b4fa6d4d97b8f097b69462f4d0
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07435837B2

Reaction notes

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