Diisopropylamine → HCID 69565593, compound

HRID 720275

Reaction equation

HRID 720275 reaction equation
[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]

Participants

8

Reactant 4

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

Product 1

HCID 69565593HCID 69565593, compoundYield 49.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-b6ba4b3a91be47418f1221e56ede1a1e
Source dataset
uspto-grants-2006_11
Patent number
US07135476B2

Linked notes

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