4-Toluenesulfonyl chloride → (2S*)-3-[(1R*,4S*)-5-(benzyloxy)-8-methoxy-1,2,3,4-tetrahydro-1,4-methanonaphthalen-6-yl]-2-hydroxypropyl 4-methylbenzenesulfonate

HRID 13934Notes

Reaction equation

HRID 13934 reaction equation
[CH2:1]([O:8][C:9]1[C:18]([CH2:19][C@H:20]([OH:23])[CH2:21][OH:22])=[CH:17][C:16]([O:24][CH3:25])=[C:15]2[C:10]=1[C@@H:11]1[CH2:26][C@H:14]2[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:27]1([CH3:37])[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1>N1C=CC=CC=1>[CH3:37][C:27]1[CH:32]=[CH:31][C:30]([S:33]([O:22][CH2:21][C@@H:20]([OH:23])[CH2:19][C:18]2[C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[C:10]3[C:15](=[C:16]([O:24][CH3:25])[CH:17]=2)[C@H:14]2[CH2:26][C@@H:11]3[CH2:12][CH2:13]2)(=[O:35])=[O:34])=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 68583362HCID 68583362, compound

Product 1

HCID 86598550(2S*)-3-[(1R*,4S*)-5-(benzyloxy)-8-methoxy-1,2,3,4-tetrahydro-1,4-methanonaphthalen-6-yl]-2-hydroxypropyl 4-methylbenzenesulfonate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Treatment of (2S*)-3-[(1R*,4S*)-5-(benzyloxy)-8-methoxy-1,2,3,4-tetrahydro-1,4-methanonaphthalen-6-yl]propane-1,2-diol (13.95 g, 39.56 mmol) with p-toluenesulfonyl chloride (8.25 g, 43.92 mmol) in anhydrous pyridine (350 mL) generally according to the procedure described for Intermediate 18 gave (2S*)-3-[(1R*,4S*)-5-(benzyloxy)-8-methoxy-1,2,3,4-tetrahydro-1,4-methanonaphthalen-6-yl]-2-hydroxypropyl 4-methylbenzenesulfonate. Treatment of the tosylate with palladium on carbon (10 wt. %, 1.6 g) generally according to the procedure described for Intermediate 4 provided 12.77 g (77%) of (2S*)-2-hydroxy-3-[(1R*,4S*)-5-hydroxy-8-methoxy-1,2,3,4-tetrahydro-1,4-methanonaphthalen-6-yl]propyl 4-methylbenzenesulfonate. Treatment of the phenyl (12.73 g, 30.4 mmol) with triphenylphosphine (8.78 g, 33.5 mmol) followed by diethylazodicarboxylate (5.83 g, 33.5 mmol) generally according to the procedure described for Intermediate 5 afforded 7.67 g (48%) of [(2R*,6R*,9S*)-5-methoxy-2,3,6,7,8,9-hexahydro-6,9-methanonaphtho[1,2-b]furan-2-yl]methyl 4-methylbenzenesulfonate as a colorless oil. Anal. calcd. for C22H24O5S: C, 65.98; H, 6.04. Found: C, 65.61; H, 5.92.

Sources & evidence

ORD record
ord-2d3cefdef0d148e68e7268acb262d204
Source dataset
uspto-grants-2010_06
Patent number
US07728155B2

Reaction notes

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