1-Naphthalenemethanamine → N-(6,6-dimethyl-2-hepten-4-ynyl)-1-naphthalenemethanamine

HRID 580006노트

반응식

HRID 580006 반응식
[C:1]1([CH2:11][NH2:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH3:13][C:14]([CH3:22])([CH3:21])[C:15]#[C:16][CH:17]=[CH:18][CH:19]=O.[BH4-].[Na+]>C(OCC)C.CO>[CH3:13][C:14]([CH3:22])([CH3:21])[C:15]#[C:16][CH:17]=[CH:18][CH2:19][NH:12][CH2:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

참가 물질

6

반응물 3

HCID 83551-NaphthalenemethanamineHCID 4311764Sodium borohydrideHCID 539349696,6-Dimethyl-2-hepten-4-ynal

생성물 1

HCID 188542N-(6,6-dimethyl-2-hepten-4-ynyl)-1-naphthalenemethanamine

시약·촉매·용매 2

HCID 887Methanol용매HCID 3283Diethyl Ether용매

실험 절차

A mixture of 1-naphthalenemethanamine (1.34 g, 8.51 mmol) and 6,6-dimethyl-2-hepten-4-ynal (1.16 g, 8.51 mmol) in 20 ml of dry ethyl ether was stirred over 4A sieves overnight. Sieve material was then removed by centrifugation, washed once with ethyl ether and the combined ether fractions concentrated to afford the crude condensed product. About 8.08 mmol of this material was stirred with sodium borohydride (343 mg, 9.06 mmol) in 20 ml of methanol at room temperature for 3.75 hours. The reaction mixture was partitioned between aqueous sodium bicarbonate and methylene chloride, the aqueous layer extracted twice with methylene chloride, and the combined organic solution washed with water and dried over magnesium sulfate. Removal of the solvent afforded N-(6,6-dimethyl-2-hepten-4-ynyl)-1-naphthalenemethanamine as a mixture of the E and Z isomers. Flash chromatography of this product on silica gel (5 cm column, eluting with 0.2% triethylamine in chloroform) afforded 0.74 g of the pure (E)-N-6,6-dimethyl-2-hepten-4-ynyl)-1-naphthalenemethanamine.

후처리

  1. customSieve material was then removed by centrifugation
  2. washwashed once with ethyl ether
  3. concentrationthe combined ether fractions concentrated
  4. customto afford the crude
  5. customcondensed product
  6. customThe reaction mixture was partitioned between aqueous sodium bicarbonate and methylene chloride
  7. extractionthe aqueous layer extracted twice with methylene chloride
  8. washthe combined organic solution washed with water
  9. dry with materialdried over magnesium sulfate
  10. customRemoval of the solvent

출처 및 근거

ORD 기록
ord-035b5a0b6e994094b2b499944d86fded
출처 데이터셋
uspto-grants-1988_06
특허 번호
US04751245

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