Dichloromethane → HCID 21404981, compound

HRID 267887Notes

Reaction equation

HRID 267887 reaction equation
C[O:2][C:3]1[CH:22]=[CH:21][C:6]([CH2:7][NH:8][C:9]([C:11]23[CH2:20][CH:15]4[CH2:16][CH:17]([CH2:19][CH:13]([CH2:14]4)[CH2:12]2)[CH2:18]3)=[O:10])=[CH:5][CH:4]=1.C(Cl)Cl.B(I)(I)I>C(OCC)(=O)C>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][NH:8][C:9]([C:11]23[CH2:12][CH:13]4[CH2:19][CH:17]([CH2:16][CH:15]([CH2:14]4)[CH2:20]2)[CH2:18]3)=[O:10])=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 83546Borane, triiodo-HCID 3120174HCID 3120174, compound

Product 1

HCID 21404981HCID 21404981, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 3.0 g. of N-(4-methoxybenzyl)-1-adamantanecarboxamide in 25 ml. of methylene chloride and cool the solution to about -78°C. Add 2.6 g. of boron triiodide and allow the reaction mixture to warm up to about 0°C with vigorous stirring. Stir the reaction mixture at about 0°C overnight, then follow the procedure described in Example 6B and crystallize the residue obtained thereby from ethyl acetate to obtain the product of this Example, m.p. 196°-198°C.

Workup

  1. dissolutionDissolve 3.0 g
  2. additionAdd 2.6 g
  3. customcrystallize the residue
  4. customobtained

Sources & evidence

ORD record
ord-c471b3503b4b43a2a83ab04fb79926fb
Source dataset
uspto-grants-1976_03
Patent number
US03944675

Reaction notes

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