Hydrogen Peroxide → HCID 69956726, compound

HRID 1937137Notes

Reaction equation

HRID 1937137 reaction equation
[CH3:1][O:2][C@H:3]1[C@@H:7]2[CH2:8][C@H:9]3[C@H:14]([C:15](=[CH2:16])[C@@H:6]2[C@@H:5]([CH3:17])[O:4]1)[CH2:13][CH2:12][CH2:11][CH2:10]3.[OH:18]O.[OH-:20].[Na+]>>[OH:18][CH2:16][C@@H:15]1[C@H:6]2[C@H:7]([C@H:3]([O:2][CH3:1])[O:4][C@@H:5]2[CH3:17])[CH2:8][C@H:9]2[C@H:14]1[CH2:13][CH2:12][CH2:11][CH2:10]2.[OH:20][CH2:16][C@H:15]1[C@H:6]2[C@H:7]([C@H:3]([O:2][CH3:1])[O:4][C@@H:5]2[CH3:17])[CH2:8][C@H:9]2[C@H:14]1[CH2:13][CH2:12][CH2:11][CH2:10]2

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 69957465HCID 69957465, compound

Product 2

HCID 69956726HCID 69956726, compoundYield 75%HCID 69957181HCID 69957181, compoundYield 8%

Procedure

Similarly to Example 8, after 663.7 mg(2.81 mmol) of (1R,3R,3aR,4aR,8aS,9aR)-1-methoxy-3-methyl-4-methylene-dodecahydronaphtho[2,3-c]furan were reacted with 4.21 ml (1.5 equivalents) of borane-tetrahydrofuran complex(1M), it was oxidized by adding 3.00 ml of 30% hydrogen peroxide solution and 3.00 ml of 10% aqueous solution of sodium hydroxide to obtain 538.2 mg of (1R,3R,3aS,4S,4aR,8aS,9aR)-4-hydroxymethyl-1-methoxy-3-methyl-dodecahydronaphtho[2,3-c]furan(yield 75%) and 55.2 mg of (1R,3R,3aS,4R,4aR,8aS,9aR)-4-hydroxymethyl-1-methoxy-3-methyl-dodecahydronaphtho[2,3-c]furan(8%). (1R,3R,3aS,4S,4aR,8aS,9aR)-4-hydoxymethyl-1-methoxy-3-methyl-dodecahydronaphtho[2,3-c]furan

Sources & evidence

ORD record
ord-19c4b8856bf24fa2915e26ff6aab40ae
Source dataset
uspto-grants-2002_05
Patent number
US06392059B1

Reaction notes

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