Citric Acid → HCID 178453956, compound

HRID 855770Notes

Reaction equation

HRID 855770 reaction equation
[BH4-].[Li+].[C:3]([O:7][C:8]([NH:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([C:17](OC)=[O:18])[CH2:13][CH2:12]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].C(O)(=O)CC(CC(O)=O)(C(O)=O)O.[OH-].[Na+]>C(OC)(C)(C)C.O1CCCC1>[OH:18][CH2:17][C@H:14]1[CH2:13][CH2:12][C@H:11]([NH:10][C:8](=[O:9])[O:7][C:3]([CH3:5])([CH3:4])[CH3:6])[CH2:16][CH2:15]1

Participants

7

Reactant 4

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 4148881Lithium borohydrideHCID 178501239HCID 178501239, compound

Product 1

HCID 178453956HCID 178453956, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 15413tert-Butyl methyl etherSolvent

Procedure

1.56 g lithium borohydride are placed in 25 ml abs. tetrahydrofuran. A solution of 15.9 g (61 mmol) methyl trans-4-tert-butoxycarbonylamino-cyclohexanecarboxylate in 25 ml abs. tetrahydrofuran is added dropwise to this suspension. This suspension is refluxed for 50 min. After the reaction mixture has cooled it is carefully added dropwise to 25 ml of 0.6 N citric acid solution. Then 30 ml tert-butylmethylether are added, the solution is made alkaline with sodium hydroxide solution and the organic phase is separated off, washed and evaporated down.

Workup

  1. temperatureThis suspension is refluxed for 50 min
  2. temperatureAfter the reaction mixture has cooled it
  3. customthe organic phase is separated off
  4. washwashed
  5. customevaporated down

Sources & evidence

ORD record
ord-7260e64429264d5bace8adedd6e9980e
Source dataset
uspto-grants-2007_08
Patent number
US07262206B2

Reaction notes

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