Trimethyl orthoformate → HCID 59129101, 화합물

HRID 2390499노트

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HRID 2390499 반응식
[CH2:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[C:11]([OH:12])[C:6]=2[CH2:5][CH2:4][NH:3][CH2:2]1.[CH3:13][C:14]([CH3:18])([CH3:17])[CH:15]=O.C(OC)(OC)OC.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CN1CCCC1=O.C(O)(=O)C>[CH2:13]([N:3]1[CH2:4][CH2:5][C:6]2[C:11]([OH:12])=[CH:10][CH:9]=[CH:8][C:7]=2[CH2:1][CH2:2]1)[C:14]([CH3:18])([CH3:17])[CH3:15]

참가 물질

7

반응물 4

HCID 9005Trimethyl orthoformateHCID 12417PivalaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 13338341HCID 13338341, 화합물

생성물 1

HCID 59129101HCID 59129101, 화합물

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

A mixture of 2,3,4,5-tetrahydro-1H-benzo[d]azepin-6-ol (see Demarinis et al. J. Med. Chem. 1984, 27, 918-921) (60 mg, 0.37 mmol), trimethylacetaldehyde (400 μL, 3.7 mmol), trimethyl orthoformate (390 μL, 3.7 mmol) and glacial acetic acid (40 μL) in 1-methyl-2-pyrrolidinone (2.5 mL) was stirred at rt for 2.5 h. Sodium triacetoxyborohydride (388 mg, 1.8 mmol) was then added and the mixture was stirred at room temperature for 16 h. The mixture was then loaded on top of a silica gel-SCX (sulfonic acid) column and eluted first with methanol, then with 2 M ammonia in methanol. The latter fraction was evaporated and the resulting 3-neopentyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-6-ol was used in the next step without further purification. (M+H)+=234.0.

후처리

  1. stirringthe mixture was stirred at room temperature for 16 h
  2. washeluted first with methanol
  3. customThe latter fraction was evaporated
  4. customthe resulting 3-neopentyl-2,3,4,5-tetrahydro-1H-benzo[d]azepin-6-ol was used in the next step without further purification

출처 및 근거

ORD 기록
ord-1cdebf125cf7474c9e6b25ef859476ff
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08273772B2

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