Trimethyl orthoformate → HCID 59129101、化合物

HRID 1991374ノート

反応式

HRID 1991374 の反応式
[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]

参加物

7

反応物 4

HCID 9005Trimethyl orthoformateHCID 12417PivalaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 13338341HCID 13338341、化合物

生成物 1

HCID 59129101HCID 59129101、化合物

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

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-pyrolidinone (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.

後処理

  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

出典と根拠

ORDレコード
ord-4feabb8b311149d3ae7f36ffa03a02d9
出典データセット
uspto-grants-2010_01
特許番号
US07645778B2

反応ノート

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