Thiophenol → HCID 69957838, compound

HRID 1937138Notes

Reaction equation

HRID 1937138 reaction equation
O[CH2:2][C@@H:3]1[C@H:15]2[C@H:11]([C@H:12]([O:17][CH3:18])[O:13][C@@H:14]2[CH3:16])[CH2:10][C@H:9]2[C@H:4]1[CH2:5][CH2:6][CH2:7][CH2:8]2.[CH3:19][S:20](Cl)(=[O:22])=[O:21].C(N(CC)CC)C.CC(C)([O-])C.[K+].[C:37]1(S)[CH:42]=[CH:41]C=[CH:39][CH:38]=1.ClC1C=CC=C(C(OO)=O)C=1.C(=O)([O-])O.[Na+]>CN(C)C1C=CN=CC=1>[CH3:18][O:17][C@H:12]1[C@@H:11]2[CH2:10][C@H:9]3[C@H:4]([C@H:3]([CH2:2][S:20]([C:19]4[CH:41]=[CH:42][CH:37]=[CH:38][CH:39]=4)(=[O:22])=[O:21])[C@@H:15]2[C@@H:14]([CH3:16])[O:13]1)[CH2:5][CH2:6][CH2:7][CH2:8]3

Participants

9

Reactant 7

HCID 7969ThiophenolHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 23665647Potassium tert-butoxideHCID 69956726HCID 69956726, compound

Product 1

HCID 69957838HCID 69957838, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

similarly to Referential example 1, 532.4 mg(2.09 mmol) of (1R,3R,3aS,4S,4aR,8aS,9aR)-4-hydroxymethyl-1-methoxy-3-methyl-dodecahydronaphtho[2,3-c]furan were mesylated with 486.0 μl(3 equivalents) of methanesulfonyl chloride, 1458.6 μl (5 equivalents) of triethylamine and 23.5 mg(0.1 equivalent) of 4-(dimethylamino)pyridine to obtain 687.5 mg of yellow oily O-mesyl form. Then, this was converted to phenylthio form with 348.1 mg(1.5 equivalents) of potassium t-butoxide and 318,5 μl (1.5 equivalents) of thiophenol and further oxidized with 1290.0 mg(2.5 equivalents) of m-chloroperbenzoic acid(70%) and 879.2 mg(5 equivalents) of sodium hydrogencarbonate to obtain 311.2 mg of (1R,3R,3aR,4S,4aR,8aS,9aR)-1-methoxy-3-methyl-4-(phenylsulfonyl)methyl-dodecahydronaphtho[2,3-c]furan(yield after 3 processes 39%).

Workup

  1. customto obtain 687.5 mg of yellow oily O-mesyl form

Sources & evidence

ORD record
ord-70c0c2c67bd04b49b5ccd4b4f349530e
Source dataset
uspto-grants-2002_05
Patent number
US06392059B1

Reaction notes

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