Diisopropylamine → HCID 69565593, 화합물

HRID 720275

반응식

HRID 720275 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

HCID 69565593HCID 69565593, 화합물수율 49.3%

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-b6ba4b3a91be47418f1221e56ede1a1e
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07135476B2

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