Sodium Hydroxide → HCID 56594895, compound

HRID 1444689Notes

Reaction equation

HRID 1444689 reaction equation
N[C@@H]1CCCC2C=C(CO)C=CC1=2.[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:20][O:21][C:22]([C:24]1[CH:33]=[CH:32][C:31]2[CH:30]([N:34]=[N+:35]=[N-:36])[CH2:29][CH2:28][CH2:27][C:26]=2[CH:25]=1)=[O:23].[OH-].[Na+]>C1COCC1.O>[CH3:20][O:21][C:22]([C:24]1[CH:33]=[CH:32][C:31]2[C@H:30]([N:34]=[N+:35]=[N-:36])[CH2:29][CH2:28][CH2:27][C:26]=2[CH:25]=1)=[O:23]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 16108956[(5R)-5-Amino-5,6,7,8-tetrahydronaphthalen-2-yl]methanolHCID 208244765-Azido-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid methyl esterHCID 21226445Aluminium lithium hydride

Product 1

HCID 56594895HCID 56594895, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent4×

Procedure

Preparation (5(R)-Amino-5,6,7,8-tetrahydro-naphthalen-2-yl)-methanol: To an oven-dried, 3-neck, 2 L round-bottomed flask equipped with argon inlet/outlet, addition funnel, thermometer, and overhead stirring was added 700 mL of THF and LAH (470 mL of a 1M soln in THF, 470 mmol, Aldrich). The reaction was cooled in a ice-salt bath, and 5-azido-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid methyl ester (27 g, 120 mmol) in 100 mL of THF was added over ca. 30 min. The mixture was warmed to RT overnight, then cooled in an ice-salt bath the next morning. Water (18 mL) in THF (20 mL) was added to the reaction mixture over 4 h. Vigorous gas evolution occurred. 5M NaOH (18 mL) was added over 30 min followed by 54 mL of water. After stirring for an additional 1 h, the mixture was filtered, and the filtrate was concentrated in vacuo. The residue was reconstituted in MeOH and CH3CN, and concentrated in vacuo again to provide the title compound as light-brown solid. MS (+ ion ESI) m/z=161 (M-NH3).

Workup

  1. customTo an oven-dried, 3-neck, 2 L round-bottomed flask equipped with argon inlet/outlet, addition funnel
  2. temperatureThe reaction was cooled in a ice-salt bath
  3. temperaturecooled in an ice-salt bath the next morning
  4. stirringAfter stirring for an additional 1 h
  5. filtrationthe mixture was filtered
  6. concentrationthe filtrate was concentrated in vacuo
  7. concentrationCH3CN, and concentrated in vacuo again

Sources & evidence

ORD record
ord-5a81583c869b4625ba83ea8a3d527812
Source dataset
uspto-grants-2010_02
Patent number
US07662811B2

Reaction notes

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