Sodium Hydroxide → HCID 12393703, compound

HRID 259011Notes

Reaction equation

HRID 259011 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([C:25](OC)=[O:26])=[C:11]2[C:16](=[CH:17][CH:18]=1)[C@@H:15]([OH:19])[C@H:14]([NH:20][CH:21]1[CH2:24][CH2:23][CH2:22]1)[CH2:13][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O1CCCC1>[CH2:1]([O:8][C:9]1[C:10]([CH2:25][OH:26])=[C:11]2[C:16](=[CH:17][CH:18]=1)[C@@H:15]([OH:19])[C@H:14]([NH:20][CH:21]1[CH2:24][CH2:23][CH2:22]1)[CH2:13][CH2:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 12393676HCID 12393676, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 12393703HCID 12393703, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 20 ml. of anhydrous tetrahydrofuran is dissolved 535 mg. of trans-6-benzyloxy-2-cyclobutylamino-1-hydroxy-5-methoxycarbonyl-1,2,3,4-tetrahydronaphthalene and with the addition of 200 mg. of lithium aluminum hydride, the solution is refluxed in a current of molecular nitrogen for 4 hours. After cooling, a 20 % solution of sodium hydroxide is added, followed by extraction with ethyl acetate. The ethyl acetate layer is washed with water, dried and concentrated under reduced pressure. The residue is recrystallized from ethyl acetate. The procedure provides trans-6-benzyloxy-2-cyclobutylamino-1-hydroxy-5-hydroxymethyl-1,2,3,4-tetrahydronaphthalene as colorless platelets melting at 156°-158° C. Yield 377 mg.

Workup

  1. temperatureAfter cooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe ethyl acetate layer is washed with water
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-74d5b7af7b7143a7b670accb48aeb355
Source dataset
uspto-grants-1977_07
Patent number
US04035512

Reaction notes

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