Diisopropylamine → HCID 69565593、化合物

HRID 720275

反応式

HRID 720275 の反応式
[CH3:1][O:2][C:3]([CH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6]1)=[O:4].[CH:14]([N-]C(C)C)(C)C.[Li+].C(NC(C)C)(C)C.Br[CH2:30][CH2:31][CH2:32][CH2:33][C:34]([O:36][CH3:37])=[O:35]>C1COCC1.O.CCOCC>[CH3:1][O:2][C:3]([C:5]1([CH2:30][CH2:31][CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:14])=[O:35])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7][CH2:6]1)=[O:4]

参加物

8

反応物 4

HCID 7912DiisopropylamineHCID 79557Methyl 5-bromovalerateHCID 2724682Lithium diisopropylamideHCID 3839612Methyl 2,3-dihydro-1H-indene-1-carboxylate

生成物 1

HCID 69565593HCID 69565593、化合物収率 49.3%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Indan-1-carboxylic acid methyl ester (17.6 g, 100 mmol) in 100 mL of THF was slowly added to a −60° C. solution of lithium diisopropylamide (from 15.4 mL (110 mmol) of diisopropylamine and 42 mL of 2.5M n-BuLi in hexane) in 200 mL of THF. After 15 min, methyl 5-bromopentanoate (20.5 g, 105 mmol) was added and the mixture was allowed to warm to room temperature and stirred for 12 h. Ether and water were added and the ether layer was separated, washed with water and brine, dried and evaporated. Purification by flash chromatography (10% ethyl acetate/hexane) afforded 15 g of 1-(4-ethoxycarbonyl-butyl)-indan-1-carboxylic acid methyl ester as an oil.

後処理

  1. customthe ether layer was separated
  2. washwashed with water and brine
  3. customdried
  4. customevaporated
  5. customPurification by flash chromatography (10% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-b6ba4b3a91be47418f1221e56ede1a1e
出典データセット
uspto-grants-2006_11
特許番号
US07135476B2

関連ノート

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