Triethylamine → HCID 86614066, compound

HRID 1727228Notes

Reaction equation

HRID 1727228 reaction equation
[C:1]([O:4][C@H:5]1[C@@H:14]2[O:15][C:16]([CH3:19])([CH3:18])[O:17][C@:13]32[C@H:8]([C@H:9]([C:21](=[O:23])[CH3:22])[CH2:10][CH2:11][C@@H:12]3[CH3:20])[CH:7]=[C:6]1[CH3:24])(=[O:3])[CH3:2].C(N(CC)CC)C.C[Si](OS(C(F)(F)F)(=O)=O)(C)C.[Br:44]N1C(=O)CCC1=O>C(OCC)C>[C:1]([O:4][C@H:5]1[C@@H:14]2[O:15][C:16]([CH3:18])([CH3:19])[O:17][C@@:13]32[C@H:8]([C@H:9]([C:21](=[O:23])[CH2:22][Br:44])[CH2:10][CH2:11][C@H:12]3[CH3:20])[CH:7]=[C:6]1[CH3:24])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 65367Trimethylsilyl triflateHCID 67184N-bromobutanimideHCID 69058233HCID 69058233, compound

Product 1

HCID 86614066HCID 86614066, compoundYield 81.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred, cooled (0° C.) solution of the product of (3aS,4R,6aS,7R,10S,10aS)-7-acetyl-2,2,5,10-tetramethyl-4,6a,7,8,9,10-hexahydro-3aH-naphtho[1,8a-d][1,3]dioxol-4-yl acetate (Preparation 148, 1.8 g) in diethyl ether (30 ml) was added triethylamine (1.8 ml) and trimethylsilyltrifluoromethanesulfonate (2.3 ml). After 30 minutes, N-bromosuccinimide (1.2 g) was added and the reaction mixture was allowed to warm to room temperature over three hours. The reaction mixture was partitioned between saturated aqueous sodium chloride and ethyl acetate. The organic phase was dried (MgSO4), evaporated and purified by flash column chromatography on silica gel using a gradient elution ethyl acetate:hexane (1:9 to 2:8) to give the product as a gum (1.81 g).

Workup

  1. customThe reaction mixture was partitioned between saturated aqueous sodium chloride and ethyl acetate
  2. dry with materialThe organic phase was dried (MgSO4)
  3. customevaporated
  4. custompurified by flash column chromatography on silica gel using
  5. washa gradient elution ethyl acetate:hexane (1:9 to 2:8)

Sources & evidence

ORD record
ord-2af63adaaafa4eeead3631014e4d0a68
Source dataset
uspto-grants-2009_02
Patent number
US07494992B2

Reaction notes

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