Citric Acid → HCID 178445701, compound

HRID 525471Notes

Reaction equation

HRID 525471 reaction equation
[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([O:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH2:18][CH:17]([CH:22]=O)[CH2:16][CH2:15]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[NH:24]1[CH2:29][CH2:28][CH:27]([C:30]([OH:32])=[O:31])[CH2:26][CH2:25]1.C(O)C.C([BH3-])#N.[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>>[C:1]([C@H:5]1[CH2:6][CH2:7][C@H:8]([O:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH2:18][CH:17]([CH2:22][N:24]2[CH2:29][CH2:28][CH:27]([C:30]([OH:32])=[O:31])[CH2:26][CH2:25]2)[CH2:16][CH2:15]3)[CH2:9][CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 5

HCID 311Citric AcidHCID 702EthanolHCID 37734-Piperidinecarboxylic acidHCID 5003444Sodium cyanoborohydrideHCID 178445702HCID 178445702, compound

Product 1

HCID 178445701HCID 178445701, compound

Procedure

A solution of 6-(trans-4-tert-butyl-cyclohexyloxy)-1,2,3,4-tetrahydro-naphthalene-2-carbaldehyde (34.5 mg, 0.110 mmol) and piperidine-4-carboxylic acid (14.2 mg, 0.110 mmol) in ethanol (0.8 mL, 10 mmol) was heated to reflux for 2 h. The yellow solution was cooled to room temperature and sodium cyanoborohydride (8.27 mg, 0.132 mmol) was added and heated to reflux for 1 h. After cooled down to room temperature, citric acid was added and concentrated down. The solid was suspended in water and filtered and the collected solid was washed thoroughly with water. HPLC purification of the solid gave the product (1.6 mg (3.4%). LCMS Rt=1.76 min, m/z=428.42 [M+1]. 1H NMR (400 MHz, METHANOL-d4) δ ppm 0.91 (s, 9H), 1.02-1.48 (m, 10H), 1.80-2.47 (m, 11H), 2.47-3.01 (m, 3H), 3.66-3.96 (m, 3H), 4.07-4.26 (m, 1H), 6.67-6.83 (m, 2H), 6.99-7.15 (m, 1H).

Workup

  1. temperatureto reflux for 2 h
  2. temperatureheated
  3. temperatureto reflux for 1 h
  4. temperatureAfter cooled down to room temperature
  5. concentrationconcentrated down
  6. filtrationfiltered
  7. washthe collected solid was washed thoroughly with water
  8. customHPLC purification of the solid
  9. customgave the product (1.6 mg (3.4%)

Sources & evidence

ORD record
ord-f78aa4a662994a86b5d42bc6fd5c311a
Source dataset
uspto-grants-2016_05
Patent number
US09340527B2

Reaction notes

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