2,2,3,3-Tetramethylcyclopropane-1-carbonyl chloride → HCID 56994894, compound

HRID 400160Notes

Reaction equation

HRID 400160 reaction equation
[Si:1]([O:8][C@H:9]1[CH2:18][C@H:17]([OH:19])[C@H:16]2[C:11]([CH:12]=[CH:13][C@H:14]([CH3:37])[C@@H:15]2[CH2:20][CH2:21][C@H:22]2[O:27][C:26](=[O:28])[CH2:25][C@H:24]([O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[CH2:23]2)=[CH:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:38][C:39]1([CH3:47])[C:41]([CH3:43])([CH3:42])[CH:40]1[C:44](Cl)=[O:45]>>[Si:1]([O:8][C@H:9]1[CH2:18][C@H:17]([O:19][C:44]([CH:40]2[C:41]([CH3:43])([CH3:42])[C:39]2([CH3:47])[CH3:38])=[O:45])[C@H:16]2[C:11]([CH:12]=[CH:13][C@H:14]([CH3:37])[C@@H:15]2[CH2:20][CH2:21][C@H:22]2[O:27][C:26](=[O:28])[CH2:25][C@H:24]([O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:31])[CH3:32])[CH2:23]2)=[CH:10]1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 110410022,2,3,3-Tetramethylcyclopropane-1-carbonyl chlorideHCID 14600906Pravastatin Diol Lactone Di-(tert-butyldimethylsilyl) Ether

Product 1

HCID 56994894HCID 56994894, compoundYield 68.5%

Procedure

A procedure similar to that described in Example 4, above, was followed, but using 1.0 g (1.8 mmol) of (4R,6R)-6-{2-[(1S,2S,6S,8S,8aR)-1,2,6,7,8,8a-hexahydro-6-t-butyldimethylsilyloxy-8-hydroxy-2-methyl-1-naphthyl]ethyl}tetrahydro-4-t-butyldimethylsilyloxy-2H-pyran-2-one [prepared as described in Example B, above], and 1.17 g of 2,2,3,3-tetramethylcyclopropanecarbonyl chloride, to provide 833 mg of the title compound.

Sources & evidence

ORD record
ord-9d8aa677f5324271adc933b21bac1187
Source dataset
uspto-grants-1998_10
Patent number
US05827855

Reaction notes

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