Diisopropylethylamine → (S)-3-(tert-butyldiphenylsilyloxy)-N1-(1-adamantylmethyl)propane-1,2-diamine

HRID 75159Notes

Reaction equation

HRID 75159 reaction equation
Cl.[NH2:2][C@@H:3]([CH2:6][NH:7][CH2:8][C:9]12[CH2:18][CH:13]3[CH2:14][CH:15]([CH2:17][CH:11]([CH2:12]3)[CH2:10]1)[CH2:16]2)[CH2:4][OH:5].CCN(C(C)C)C(C)C.[CH3:28][C:29]([Si:32](Cl)([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([CH3:31])[CH3:30]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Si:32]([O:5][CH2:4][C@@H:3]([NH2:2])[CH2:6][NH:7][CH2:8][C:9]12[CH2:18][CH:13]3[CH2:12][CH:11]([CH2:17][CH:15]([CH2:14]3)[CH2:16]1)[CH2:10]2)([C:29]([CH3:31])([CH3:30])[CH3:28])([C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 94078tert-ButyldiphenylchlorosilaneHCID 68477778HCID 68477778, compound

Product 1

HCID 68474186(S)-3-(tert-butyldiphenylsilyloxy)-N1-(1-adamantylmethyl)propane-1,2-diamineYield 34.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-2-amino-3-((1-adamantylmethyl)amino)propan-1-ol HCl salt (1.2 g, 3.8 mmol) in anhydrous CH2Cl2 (20 mL) were added DIEA (1.9 g, 15.2 mmol), DMAP (2.3 mg, 0.02 mmol) and TBDPSCl (1.2 g, 4.2 mmol) at 0° C. The mixture was stirred at rt for 2 h. The reaction solution was extracted with CH2Cl2 (100 mL) and water (20 mL). The organic layer was washed with brine (20 mL), dried over MgSO4, and concentrated to give the crude product, which was purified by preparative TLC (PE:EtOAc 10/1) to afford (S)-3-(tert-butyldiphenylsilyloxy)-N1-(1-adamantylmethyl)propane-1,2-diamine (620 mg, 29%) 1H NMR: (CDCl3, 400 MHz): δ=1.05 (s, 9H), 1.54 (s, 6H), 1.62-1.73 (m, 6H), 1.98 (s, 3H), 2.32 (d, 1H), 2.45 (d, 1H), 2.56 (d, 1H), 2.85 (d, 1H), 3.15 (m, 4H), 3.65 (m, 2H), 7.4 (m, 6H), 7.62 (m, 4H).

Workup

  1. extractionThe reaction solution was extracted with CH2Cl2 (100 mL) and water (20 mL)
  2. washThe organic layer was washed with brine (20 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customto give the crude product, which
  6. customwas purified by preparative TLC (PE:EtOAc 10/1)

Sources & evidence

ORD record
ord-c3e7ace0c19f4e1d9e9d57f0aadba26a
Source dataset
uspto-grants-2014_09
Patent number
US08835426B2

Reaction notes

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