Potassium sodium tartarate → HCID 22467287, compound

HRID 1934555Notes

Reaction equation

HRID 1934555 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Si:7]([O:24][C:25]1[CH:34]=[CH:33][CH:32]=[C:31]2[C:26]=1[CH2:27][CH2:28][CH2:29][C:30]2([O:37][Si](C)(C)C)[C:35]#[N:36])([C:20]([CH3:23])([CH3:22])[CH3:21])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1COCC1>[NH2:36][CH2:35][C:30]1([OH:37])[C:31]2[C:26](=[C:25]([O:24][Si:7]([C:20]([CH3:22])([CH3:21])[CH3:23])([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:34]=[CH:33][CH:32]=2)[CH2:27][CH2:28][CH2:29]1

Participants

5

Reactant 3

HCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydrideHCID 22467314HCID 22467314, compound

Product 1

HCID 22467287HCID 22467287, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (6.12 g) in THF (450 ml) was dropwise added a solution of crude 5-(tert-butyldiphenylsilyloxy)-1-trimethylsilyloxy-1,2,3,4-tetrahydronaphthalene-1-carbonitrile (40.3 g) in THF (300 ml) at 5° C. The mixture was stirred at the same temperature for 1 hour and then at room temperature for 2 hours. The mixture was added with a saturated potassium sodium tartrate solution under ice cooling. A resultant insoluble material was removed by filtration and washed with THF. The filtrate was evaporated to give 1-aminomethyl-5-(tert-butyldiphenylsilyloxy)-1,2,3,4-tetrahydronaphthalen-1-ol (34.8 g) as an oil.

Workup

  1. waitat room temperature for 2 hours
  2. customA resultant insoluble material was removed by filtration
  3. washwashed with THF
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-b21130aa6b644ea1909f1623087811cf
Source dataset
uspto-grants-2002_05
Patent number
US06384072B1

Reaction notes

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