Water → 1-(2-methyl-1,3-dioxolan-2-yl-methyl)-9-methoxy-3-methyl-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepine

HRID 46518Notes

Reaction equation

HRID 46518 reaction equation
C(N(CC)CC)C.[CH3:8][C:9]1([CH2:14][C:15]2[C:16](=O)[N:17]([CH3:32])[CH2:18][CH2:19][CH:20]3[CH2:29][CH2:28][C:27]4[C:22](=[CH:23][CH:24]=[C:25]([O:30][CH3:31])[CH:26]=4)[C:21]=23)[O:13][CH2:12][CH2:11][O:10]1.O.[OH-].[Na+]>C1C=CC=CC=1.O1CCCC1>[CH3:8][C:9]1([CH2:14][C:15]2[CH2:16][N:17]([CH3:32])[CH2:18][CH2:19][CH:20]3[CH2:29][CH2:28][C:27]4[C:22](=[CH:23][CH:24]=[C:25]([O:30][CH3:31])[CH:26]=4)[C:21]=23)[O:10][CH2:11][CH2:12][O:13]1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 205555911-(2-methyl-1,3-dioxolan-2-yl-methyl)-9-methoxy-3-methyl-3,4,5,5a,6,7-hexahydro-2H-naphth-[1,2-d]azepin-2-one

Product 1

HCID 205556071-(2-methyl-1,3-dioxolan-2-yl-methyl)-9-methoxy-3-methyl-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepine

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8028TetrahydrofuranSolvent

Procedure

The starting material is prepared as follows: 105 ml of a 1.1 M solution of alane-triethylamine in benzene are added dropwise to the solution of 31.2 g of 1-(2-methyl-1,3-dioxolan-2-yl-methyl)-9-methoxy-3-methyl-3,4,5,5a,6,7-hexahydro-2H-naphth-[1,2-d]azepin-2-one in 200 ml of anhydrous tetrahydrofuran at 0°. The mixture is stirred at 0° for 4 hours whereupon 44 ml of water are added slowly, followed by 88 ml of 3 N aqueous sodium hydroxide at 0°. The resulting mixture is extracted with diethyl ether, the extract dried and evaporated to give the 1-(2-methyl-1,3-dioxolan-2-yl-methyl)-9-methoxy-3-methyl-3,4,5,5a,6,7-hexahydro-2H-naphth[1,2-d]azepine.

Workup

  1. customThe starting material is prepared
  2. additionare added slowly
  3. extractionThe resulting mixture is extracted with diethyl ether
  4. customthe extract dried
  5. customevaporated

Sources & evidence

ORD record
ord-43f329a76ca1414b9f7022aedce550f9
Source dataset
uspto-grants-1979_11
Patent number
US04173633

Reaction notes

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