Triethylamine → HCID 69056915, compound

HRID 1727213Notes

Reaction equation

HRID 1727213 reaction equation
ClC1C2N(C)O[C@H]3N[C@H](C([O:18][C@@H:19]4[C@:28]5([OH:29])[C@H:23]([C@H:24]([C:31]([CH3:33])=[CH2:32])[CH2:25][CH2:26][C@H:27]5[CH3:30])[CH:22]=[C:21]([CH3:34])[C@H:20]4[O:35][C:36](=[O:38])[CH3:37])=O)C[C@@]3(O)C=2C=CC=1.C(N(CC)CC)C>CO>[C:36]([O:35][C@@H:20]1[C:21]([CH3:34])=[CH:22][C@H:23]2[C@@:28]([OH:29])([C@@H:27]([CH3:30])[CH2:26][CH2:25][C@H:24]2[C:31]([CH3:33])=[CH2:32])[C@H:19]1[OH:18])(=[O:38])[CH3:37]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 86614034HCID 86614034, compound

Product 1

HCID 69056915HCID 69056915, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (1S,2R,4aS,5R,8R,8aR)-2-(acetyloxy)-8a-hydroxy-3,8-dimethyl-5-(1-methylethenyl)-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl (2S,3aR,9bR)-6-chloro-9b -hydroxy-5-methyl-1,2,3,3a,5,9b-hexahydropyrrolo[2,3-c][2,1]benzoxazine-2-carboxylate, (Preparation 1, 100 g) and triethylamine (10 ml) in methanol (1000 ml) was stirred at room temperature for 3 hours. The reaction mixture was evaporated and the residue was crystallised from ethyl acetate/hexane to give a pure sample of the terpene, (1S,2R,4aR,5R,8S,8aS)-1,8a-dihydroxy-5-isopropenyl-3,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-2-naphthalenyl acetate (Preparation 126). The remaining solution was concentrated and purified by flash column chromatography on silica-gel eluting with ethyl acetate:dichloromethane:hexane (2:1:7) to give further terpene moiety (1S,2R,4aR,5R,8S,8aS)-1,8a-dihydroxy-5-isopropenyl-3,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-2-naphthalenyl acetate as a white solid (Preparation 126, 43 g).

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue was crystallised from ethyl acetate/hexane

Sources & evidence

ORD record
ord-b525d2242fe4472b8140693a4272d6ff
Source dataset
uspto-grants-2009_02
Patent number
US07494992B2

Reaction notes

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