Water → 7-tert-butoxycarbonyl-2-oxohexahydro-3,5-methano-2H-cyclopenta[b]furan-6-yl adamantanecarboxylate

HRID 926438Notes

Reaction equation

HRID 926438 reaction equation
[OH:1][CH:2]1[CH:6]2[O:7][C:8](=[O:18])[CH:9]3[CH:10]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:3]1[CH2:4][CH:5]23.C(N(CC)CC)C.[C:26]12([C:36](Cl)=[O:37])[CH2:35][CH:30]3[CH2:31][CH:32]([CH2:34][CH:28]([CH2:29]3)[CH2:27]1)[CH2:33]2.O>C(#N)C.CN(C)C1C=CN=CC=1>[C:26]12([C:36]([O:1][CH:2]3[CH:6]4[O:7][C:8](=[O:18])[CH:9]5[CH:10]([C:11]([O:13][C:14]([CH3:15])([CH3:17])[CH3:16])=[O:12])[CH:3]3[CH2:4][CH:5]45)=[O:37])[CH2:33][CH:32]3[CH2:31][CH:30]([CH2:29][CH:28]([CH2:34]3)[CH2:27]1)[CH2:35]2

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 989151-Adamantanecarbonyl chlorideHCID 57824120HCID 57824120, compound

Product 1

HCID 1181290117-tert-butoxycarbonyl-2-oxohexahydro-3,5-methano-2H-cyclopenta[b]furan-6-yl adamantanecarboxylateYield 85%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

In 2,000 ml of acetonitrile were dissolved 282 g of tert-butyl 6-hydroxy-2-oxohexahydro-3,5-methano-2H-cyclopenta[b]furan-7-carboxylate (21), 157 g of triethylamine and 13.6 g of 4-dimethylaminopyridine. Below 20° C., 328 g of adamantanecarboxylic chloride (26) was added dropwise to the solution, which was stirred at room temperature for 3 hours. Then 1,000 g of water was added to the solution, followed by standard work-up. Recrystallization from methylene chloride gave 391 g of the target compound (yield 85%).

Workup

  1. customRecrystallization from methylene chloride

Sources & evidence

ORD record
ord-4af7a88197fd4d129e4088d140f8f57f
Source dataset
uspto-grants-2016_03
Patent number
US09285678B2

Reaction notes

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