Acetic Acid → HCID 19848791, compound

HRID 1608430Notes

Reaction equation

HRID 1608430 reaction equation
[OH:1][CH2:2][CH2:3][CH:4]1[C:13]2[C:8](=[CH:9][C:10]([CH2:15][CH2:16][CH2:17][S:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:11][C:12]=2[OH:14])[NH:7][CH:6]([CH3:23])[CH2:5]1.C=O.[C:26]([BH3-])#N.[Na+].C(O)(=O)C>C(#N)C>[OH:1][CH2:2][CH2:3][CH:4]1[C:13]2[C:8](=[CH:9][C:10]([CH2:15][CH2:16][CH2:17][S:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:11][C:12]=2[OH:14])[N:7]([CH3:26])[CH:6]([CH3:23])[CH2:5]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 19848830HCID 19848830, compound

Product 1

HCID 19848791HCID 19848791, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of dl-4-(2-hydroxyethyl)-5-hydroxy-2-methyl-7-(4-thiaoctyl)-1,2,3,4-tetrahydroquinoline (337 mg, 1.0 mmole) in 5 ml acetonitrile cooled to 15° C. is added 0.5 ml aqueous formaldehyde and 100 mg sodium cyanoborohydride. Acetic acid is added to maintain a neutral pH until the reaction is complete. The reaction mixture is partitioned between water and ethyl ether, the organic phase dried (MgSO4) and evaporated to afford the title compound.

Workup

  1. temperatureto maintain a neutral pH until the reaction
  2. customThe reaction mixture is partitioned between water and ethyl ether
  3. dry with materialthe organic phase dried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-4ff7f18044cc46bca9f92a5a1de16401
Source dataset
uspto-grants-1989_09
Patent number
US04870084

Reaction notes

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