Triethylamine → (4R,6R)-6-{2-[(1S,2S,6S,8S,8aR)-1,2,6,7,8,8a-Hexahydro-6-t-butyldimethylsilyloxy-8-(2,2-diethylbutyryloxy)-2-methyl-1-naphthyl]ethyl}tetrahydro-4-t-butyldimethylsilyloxy-2H-pyran-2-one

HRID 400138Notes

Reaction equation

HRID 400138 reaction equation
[CH2:1]([C:3]([CH2:9][CH3:10])([CH2:7][CH3:8])[C:4](Cl)=[O:5])[CH3:2].[Si:11]([O:18][C@H:19]1[CH2:28][C@H:27]([OH:29])[C@H:26]2[C:21]([CH:22]=[CH:23][C@H:24]([CH3:47])[C@@H:25]2[CH2:30][CH2:31][C@H:32]2[O:37][C:36](=[O:38])[CH2:35][C@H:34]([O:39][Si:40]([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:42])[CH3:41])[CH2:33]2)=[CH:20]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].N1(C2C=CN=CC=2)CCCC1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[Si:11]([O:18][C@H:19]1[CH2:28][C@H:27]([O:29][C:4](=[O:5])[C:3]([CH2:9][CH3:10])([CH2:7][CH3:8])[CH2:1][CH3:2])[C@H:26]2[C:21]([CH:22]=[CH:23][C@H:24]([CH3:47])[C@@H:25]2[CH2:30][CH2:31][C@H:32]2[O:37][C:36](=[O:38])[CH2:35][C@H:34]([O:39][Si:40]([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:41])[CH3:42])[CH2:33]2)=[CH:20]1)([C:14]([CH3:15])([CH3:16])[CH3:17])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 755674-PyrrolidinopyridineHCID 50970172,2-diethylbutanoyl ChlorideHCID 14600906Pravastatin Diol Lactone Di-(tert-butyldimethylsilyl) Ether

Product 1

HCID 22856156(4R,6R)-6-{2-[(1S,2S,6S,8S,8aR)-1,2,6,7,8,8a-Hexahydro-6-t-butyldimethylsilyloxy-8-(2,2-diethylbutyryloxy)-2-methyl-1-naphthyl]ethyl}tetrahydro-4-t-butyldimethylsilyloxy-2H-pyran-2-oneYield 89.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.48 g (9.1 mmol) of 2,2-diethylbutyryl chloride were added to a solution of 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] 1.67 g (11.3 mmol) of 4-(1-pyrrolidinyl)pyridine and 1.0 ml (7.1 mmol) of triethylamine in 10 ml of toluene, and the resulting mixture was heated under reflux for 10 hours. At the end of this time the reaction mixture was worked-up following a procedure similar to that described in Example 5, above, to give 1.09 g (89% yield) of the title compound.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 10 hours

Sources & evidence

ORD record
ord-6dbcb520557345fbb78250ba47dfe89d
Source dataset
uspto-grants-1998_10
Patent number
US05827855

Reaction notes

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