Diisopropylethylamine → HCID 66905552, compound

HRID 1691417Notes

Reaction equation

HRID 1691417 reaction equation
Cl.[NH2:2][C@@H:3]1[C:12]([CH3:14])([CH3:13])[C:11]2[CH:10]=[C:9]([C:15]([NH2:17])=[O:16])[CH:8]=[CH:7][C:6]=2[CH2:5][C@H:4]1[O:18][CH3:19].[C:20]([O:24][C:25](=[O:31])[NH:26][CH2:27][CH2:28][CH:29]=O)([CH3:23])([CH3:22])[CH3:21].C(N(CC)C(C)C)(C)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCl>[C:20]([O:24][C:25](=[O:31])[NH:26][CH2:27][CH2:28][CH2:29][NH:2][C@H:3]1[C@H:4]([O:18][CH3:19])[CH2:5][C:6]2[C:11](=[CH:10][C:9]([C:15](=[O:16])[NH2:17])=[CH:8][CH:7]=2)[C:12]1([CH3:14])[CH3:13])([CH3:23])([CH3:22])[CH3:21]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 10910051tert-Butyl N-(3-oxopropyl)carbamateHCID 66674619HCID 66674619, compound

Product 1

HCID 66905552HCID 66905552, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

trans-7-Amino-8,8-dimethyl-6-methoxy-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid amide hydrochloride (0.75 g, 2.64 mmol), (3-oxo-propyl)-carbamic acid tert-butyl ester (0.55 g, 3.16 mmol), and N,N-diisopropylethylamine (1.38 mL, 7.92 mmol) were dissolved in dichloromethane (15 mL) at room temperature. Sodium triacetoxyborohydride (1.03 g, 4.85 mmol) was added and the reaction was stirred for 17 h at room temperature. Saturated sodium bicarbonate was added, and the reaction mixture was extracted with dichloromethane. The organic extract was dried with Na2SO4 and concentrated to give the title compound as the crude free base (1.07 g, 100% yield, 79% purity). (m/z): [M+H]+ calcd for C22H35N3O4, 406.3; found, 406.5.

Workup

  1. extractionthe reaction mixture was extracted with dichloromethane
  2. extractionThe organic extract
  3. dry with materialwas dried with Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-10aee5ff8b6549928e2d570bb83afbbc
Source dataset
uspto-grants-2012_04
Patent number
US08153686B2

Reaction notes

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