Diazomethane → (6-Amino-2-cyclopropylmethyl-3-hydroxy-phenyl)-(4-isopropyl-phenyl)methanone

HRID 1046386Notes

Reaction equation

HRID 1046386 reaction equation
[N+](=[CH2:3])=[N-].N(N(C)C(N)=O)=O.[OH-].[K+].[CH2:13]([C:16]1[C:21]([OH:22])=[CH:20][CH:19]=[C:18]([NH2:23])[C:17]=1[C:24]([C:26]1[CH:31]=[CH:30][C:29]([CH:32]([CH3:34])[CH3:33])=[CH:28][CH:27]=1)=[O:25])[CH:14]=[CH2:15]>C(OCC)C>[NH2:23][C:18]1[C:17]([C:24]([C:26]2[CH:27]=[CH:28][C:29]([CH:32]([CH3:34])[CH3:33])=[CH:30][CH:31]=2)=[O:25])=[C:16]([CH2:13][CH:14]2[CH2:3][CH2:15]2)[C:21]([OH:22])=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 9550Diazomethane2×HCID 12699N-Methyl-N-nitrosoureaHCID 14797Potassium HydroxideHCID 45141175(2-Allyl-6-amino-3-hydroxy-phenyl)-(4-isopropyl-phenyl)-methanone

Product 1

HCID 45141176(6-Amino-2-cyclopropylmethyl-3-hydroxy-phenyl)-(4-isopropyl-phenyl)methanone

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A diazomethane solution is freshly prepared by adding 515 mg (5 mmol) N-nitroso-N-methylurea in small portions to a stirred mixture of 50 ml diethyl ether and 17.5 ml 40% aqueous potassium hydroxide solution at 5° C. Ten minutes after the last addition, the organic layer is separated off and dried over solid potassium hydroxide. This diazomethane solution is added to a concentrated solution of 1.00 g (3.39 mmol) (2-allyl-6-amino-3-hydroxy-phenyl)-(4-isopropyl-phenyl)-methanone in diethyl ether containing 152 mg (0.68 mmol) Pd(OAc)2. After stirring for 16 h at r.t. the reaction mixture is filtered, evaporated to dryness and purified by flash column chromatography.

Workup

  1. additionTen minutes after the last addition
  2. customthe organic layer is separated off
  3. dry with materialdried over solid potassium hydroxide
  4. filtrationis filtered
  5. customevaporated to dryness
  6. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-ade76fd5cad74b01a1e9d1ad0a4c64c8
Source dataset
uspto-grants-2013_10
Patent number
US08569317B2

Reaction notes

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