Water → HCID 22804690, compound

HRID 2419841Notes

Reaction equation

HRID 2419841 reaction equation
O=[CH:2][CH2:3][C@@H:4]([C@@H:6]([CH2:8][OH:9])[OH:7])[OH:5].[CH2:10]([NH2:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.O.[H][H]>CO.[Pt]=O>[CH2:10]([NH:17][CH2:2][CH2:3][C@H:4]([OH:5])[C@@H:6]([OH:7])[CH2:8][OH:9])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7504BenzylamineHCID 54600052-Deoxyribose, D-HCID 178418361HCID 178418361, compound

Product 1

HCID 22804690HCID 22804690, compoundYield 59.5%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 887MethanolSolvent

Procedure

2-Deoxy-D-ribose (100 g; 0.746 mole) and benzylamine (96 g; 0.897 mole) were dissolved in methanol (400 ml) and water (40 ml) and hydrogenated at 50° C and 50 p.s.i. in the presence of platinum oxide catalyst (4.0 g) until hydrogen uptake was complete. The catalyst was filtered off and the filtrate was cooled in an ice bath. The resulting crystalline precipitate was collected, washed with cold methanol, and dried to give 5-(benzylamino)-1,2(S),3(S)-trihydroxypentane (100 g; 59.5% yield). A sample was recrystallized from ethyl acetate, m.p. 117°-118.5° C, δ (DMSO-D6) 7.3 (5H, s); 3.9 (3H, m, exchangeable with D2O); 3.7 (2H, s); 3.4 (4H, m); 2.6 (2H, m); 1.6 (2H, m). νmax. 3370, 3310, 3290 cm-1. (Found: C, 64.3; H, 8.5; N, 6.1. C12H19NO3 requires: C, 64.0; H, 8.5; N, 6.2%). (A).

Workup

  1. customhydrogenated at 50° C
  2. filtrationThe catalyst was filtered off
  3. temperaturethe filtrate was cooled in an ice bath
  4. customThe resulting crystalline precipitate was collected
  5. washwashed with cold methanol
  6. customdried

Sources & evidence

ORD record
ord-08b8154b1f7c4d4d9d9f404c48a548d9
Source dataset
uspto-grants-1978_08
Patent number
US04107435

Reaction notes

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